RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2007(6): 795-818
DOI: 10.1055/s-2007-965963
DOI: 10.1055/s-2007-965963
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Synthesizing Allenes Today (1982-2006)
Weitere Informationen
Received
14 December 2006
Publikationsdatum:
28. Februar 2007 (online)
Publikationsverlauf
Publikationsdatum:
28. Februar 2007 (online)
Abstract
Allenes have allowed chemists to access a variety of structurally interesting and biologically active products. The emergence of these unique compounds in organic synthesis is a direct result of the discovery and development of efficient protocols for their preparation. Moreover, efficient syntheses of the allenyl functionality are important to the synthetic community and will be reported and discussed in this review.
-
1 Introduction
-
2 Synthesis of Allenes with Aluminum Hydride Reagents
-
2.1 Allenes from Propargyl Electrophiles
-
2.2 Allenes from Enynes
-
3 Allene Synthesis via Skeletal Rearrangement Reactions
-
3.1 Allene Synthesis via Claisen Rearrangements
-
3.2 Allene Synthesis via Other [3,3]-Sigmatropic Rearrangements
-
3.3 Allene Synthesis via [2,3]-Sigmatropic Rearrangements
-
3.4 Allenes via Carbene Rearrangement: The Doering-Moore-Skatteböl Reaction
-
3.5 Allenes via Ene Reactions
-
4 Allene Synthesis via Direct Homologation Reactions
-
4.1 Wittig, Wittig-Horner, and Horner-Wadsworth-Emmons (HWE) Reactions
-
4.2 Peterson Allenation
-
4.3 Crabbé Homologation Reaction
-
5 Allene Synthesis via β-Elimination Reactions
-
5.1 β-Elimination of Enol Phosphates
-
5.2 β-Elimination of Sulfoxide Derivatives
-
5.3 Allenes via Deoxystannylation
-
5.4 β-Elimination via Radical Intermediates
-
5.5 Allenes from β-Chlorovinylsilanes
-
5.6 Transition-Metal-Catalyzed β-Elimination
-
6 Transition-Metal-Catalyzed Allene Synthesis
-
6.1 Palladium-Catalyzed SN2′ Substitution of Dienes
-
6.2 Palladium-Catalyzed 1,4-Addition of Enynes
-
6.3 Palladium-Catalyzed Hydrogen Transfer Reactions of Propargyl Amines
-
6.4 Palladium-Catalyzed Carbonylation Reaction of Propargyl Substrates
-
6.5 Palladium-Catalyzed Cross-Coupling of Propargyl Derivatives
-
6.6 Indium-Mediated Allene Formation
-
6.7 Chromium-Catalyzed Allene Formation
-
6.8 Ruthenium-Catalyzed Allene Formation
-
6.9 Rhodium-Catalyzed Allene Formation
-
6.10 A Zinc Carbenoid-Vinyl Copper Coupling to Form Allenes
-
6.11 Titanium-Catalyzed Allene Formation
-
6.12 Copper-Catalyzed Coupling of Allenyl Halides with Amide Derivatives
-
7 Conclusion
Key words
allenes - rearrangements - homologation - elimination - additions
- 1
Hopf H. The Preparation of Allenes and Cumulenes, In The Chemistry of Ketenes, Allenes and Related Compounds, Part 1Patai S. John Wiley & Sons; New York: 1980. p.779-901 - 2
Brandsma L.Verkrujijsse HD. Synthesis of Acetylenes Allenes and Cumulenes, Studies in Organic Chemistry 8 Elsevier; New York: 1981. - 3
Landor PD. Synthesis of Allenes, In The Chemistry of Allenes Vol. 1:Landor SR. Academic Press; New York: 1982. p.19-118 - 4
Schuster HF.Coppola GM. Allenes in Organic Synthesis John Wiley & Sons; New York: 1984. - 5
Taylor DR. Chem. Rev. 1967, 67: 317 - 6
Smadja W. Chem. Rev. 1983, 83: 263 - 7
Pasto DJ. Tetrahedron 1984, 40: 2805 - 8
Yamamoto H. Propargyl and Allenyl Organometallics, In Comprehensive Organic Synthesis Vol. 1:Trost BM.Fleming I. Pergamon Press; New York: 1991. p.81-98 - 9
Banert K. Liebigs Ann./Recl. 1997, 2005 - 10
Zimmer R. Synthesis 1993, 165 - 11
Krause N.Hoffmann-Röder A.Canisius J. Synthesis 2002, 1759 - 12
Hoffmann-Röder A.Krause N. Angew. Chem. Int. Ed. 2002, 41: 2933 - 13
Sydnes LK. Chem. Rev. 2003, 103: 1133 - 14
Wei L.-L.Xiong H.Hsung RP. Acc. Chem. Res. 2003, 36: 773 - 15
Krause N.Hoffmann-Röder A. Tetrahedron 2004, 60: 11671 - 16
Hoffmann-Röder A.Krause N. Angew. Chem. Int. Ed. 2004, 43: 1196 - 17
Miesh M. Synthesis 2004, 746 - 18
Bruneau C.Renaud J.-L. Allenes and Cumulenes, In Comprehensive Organic Functional Group Transformations II Vol. 1:Cossy J. Elsevier; Oxford: 2005. p.1019-1081 - 19
Saito S. In Science of Synthesis Vol. 7:Yamamoto H. Thieme; Stuttgart: 2004. p.15 - 20
Claesson A.Olsson L.-I. J. Am. Chem. Soc. 1979, 101: 7302 - 21
Cowie JS.Landor PD.Landor SR. J. Chem. Soc., Perkin Trans. 1 1973, 720 - 22
Kumareswaran R.Shin S.Gallou I.RajanBabu TV. J. Org. Chem. 2004, 69: 7157 - 23
Yoshida M.Komatsuzaki Y.Nemoto H.Ihara M. Org. Biomol. Chem. 2004, 2: 3099 - 24
Lautens M.Delanghe P. J. Am. Chem. Soc. 1994, 116: 8526 - 25
VanBrunt MP.Standaert RF. Org. Lett. 2000, 2: 705 - 26
Snowden RL.Linder S. Helv. Chim. Acta 2005, 88: 3055 - 27
Cao H.Flippen-Anderson J.Cook J. J. Am. Chem. Soc. 2003, 125: 3230 - 28
Bungard CJ.Morris J. J. Org. Chem. 2002, 67: 2361 - 29
Hung S.-C.Wen Y.-F.Chang J.-W.Liao C.-C.Uang B.-J. J. Org. Chem. 2002, 67: 1308 - 30
Ito M.Hirata Y.Tsukida K.Tanaka N.Hamada K.Hino R.Fujiwara TF. Chem. Pharm. Bull. 1988, 36: 3328 - 31
Yamano Y.Watanabe Y.Watanabe N.Ito M. J. Chem. Soc., Perkin Trans. 1 2002, 2833 - 32
Furuichi N.Hara H.Osaki T.Nakano M.Mori H.Katsumura S. J. Org. Chem. 2004, 69: 7949 - 33
Santelli M.Bertrand M. Bull. Soc. Chim. Fr. 1973, 2335 - 34
Evans JD.Landor SR.Regan JP. J. Chem. Soc., Perkin Trans. 1 1974, 552 - 35
Bovicelli P.Mincione E.Parsons PJ. Synth. Commun. 1988, 18: 1231 - 36
Castro AMM. Chem. Rev. 2004, 104: 2939 - 37
Trost BM.Pinkerton AB.Seidel M. J. Am. Chem. Soc. 2001, 123: 12466 - 38
Black DK.Landor SR. J. Chem. Soc. 1965, 5225 - 39
Saucy G.Marbet R. Helv. Chim. Acta 1967, 50: 1158 - 40
Ficini J.Lumbroso-Bader N.Pouliquen J. Tetrahedron Lett. 1968, 9: 4139 - 41
Zachová H.Man S.Nečas M.Potáček M. Eur. J. Org. Chem. 2005, 2548 - 42
Crandall JK.Tindell GL. J. Chem. Soc., Chem. Commun. 1970, 1411 - 43
Agami C.Couty F.Evano G. Eur. J. Org. Chem. 2002, 29 - 44
Parker KA.Petraitis JJ.Raymond W.Kosely J.Buchwald SL. J. Org. Chem. 1982, 47: 389 - 45
Parker KA.Kosely RW. Tetrahedron Lett. 1976, 17: 341 - 46
Baldwin JE.Bennett PAR.Forrest AK. J. Chem. Soc., Chem. Commun. 1987, 250 - 47
Brummond KM.You L. Tetrahedron 2005, 61: 6180 - 48
Yang Y.Petersen JL.Wang KK. J. Org. Chem. 2003, 68: 8545 - 49
Fujisawa T.Maehata E.Kohama H.Sato T. Chem. Lett. 1985, 1457 - 50
Kazmaier U.Görbitz CH. Synthesis 1996, 1489 - 51
Brummond KM.Mitasev B. Org. Lett. 2004, 6: 2245 - 52
Castelhano AL.Horne S.Talyor GJ.Billedeau R.Krantz A. Tetrahedron 1988, 44: 5451 - 53
Brummond KM.Curran DP.Mitasev B.Fischer S.
J. Org. Chem. 2005, 70: 1745 - 54
Trost B.Krishe M. J. Am. Chem. Soc. 1999, 121: 6131 - 55
Sherry BD.Toste FD. J. Am. Chem. Soc. 2004, 126: 15978 - 56
Frederick MO.Hsung RP.Lambeth RH.Mulder JA.Tracey MR. Org. Lett. 2003, 5: 2663 - 57
Kurtz KCM.Fredreick MO.Lambeth RH.Mulder JA.Tracey MR.Hsung RP. Tetrahedron 2006, 62: 3928 - 58
Bowden B.Cookson RC.Davis H. J. Chem. Soc., Perkin Trans. 1 1973, 2634 - 59
Marion N.Díez-González S.Frémont Pd.Noble AR.Nolan SP. Angew. Chem. Int. Ed. 2006, 45: 3647 - 60
Zhang L.Wang S. J. Am. Chem. Soc. 2006, 128: 1442 - 61
Cariou K.Mainetti E.Fensterbank L.Malacria M. Tetrahedron 2004, 60: 9745 - 62
Sromek AW.Kel"in AV.Gevorgyan V. Angew. Chem. Int. Ed. 2004, 43: 2280 - 63
Cookson RC.Cramp MC.Parsons PJ. J. Chem. Soc. Perkin Trans. 1 1980, 197 - 64
Zhang L. J. Am. Chem. Soc. 2005, 127: 16804 - 65
Castelhano AL.Krantz A. J. Am. Chem. Soc. 1984, 106: 1877 - 66
Harusawa S.Kase N.Yoneda R.Kurihara T. Tetrahedron Lett. 1994, 35: 1255 - 67
Harusawa S.Moriyama H.Kase N.Ohishi H.Yoneda R.Kurihara T. Tetrahedron 1995, 51: 6475 - 68
Banert K.Groth S.Hückstädt H.Lechmann J.Schlott J.Vrobel K. Synthesis 2002, 1423 - 69
Banert K.Hückstädt H.Vrobel K. Angew. Chem., Int. Ed. Engl. 1992, 31: 90 - 70
Banert K.Hagedorn M.Müller A. Eur. J. Org. Chem. 2001, 1089 - 71
Banert K.Hagedorn M. Angew. Chem., Int. Ed. Engl. 1989, 28: 1675 - 72
Banert K.Toth C. Angew. Chem., Int. Ed. Engl. 1995, 34: 1627 - 73
Macomber RS.Hemling TC. J. Am. Chem. Soc. 1986, 108: 343 - 74
Mark V. The Uncatalyzed Rearrangement of Tetravalent Phosphorous Esters, In Mechanisms of Molecular Migrations Vol. 2:Thyagarajan BS. John Wiley & Sons; New York: 1969. p.319-341 - 75
Mukai C.Ohta M.Yamashita H.Kitagaki S. J. Org. Chem. 2004, 69: 6867 - 76
González-Cantalapiedra E.Frutos Ód.Atienza C.Mateo C.Echavarren AM. Eur. J. Org. Chem. 2006, 1430 - 77
Denmark SE.Stadler H.Dorow RL.Kim J.-H. J. Org. Chem. 1991, 56: 5063 - 78
Braverman S.Kumar EVKS.Cherkinsky M.Sprecher M.Goldberg I. Tetrahedron 2005, 61: 3547 - 79
Christov VC.Ivanova JG. Synth. Commun. 2006, 36: 2231 - 80
Nakai T.Mikami K. Chem. Rev. 1986, 86: 885 - 81
Marshall JA.Robinson ED.Zapata A. J. Org. Chem. 1989, 54: 5854 - 82
Marshall JA.Yu RH.Perkins JF. J. Org. Chem. 1995, 60: 5550 - 83
Marshall JA.Wang X.-j. J. Org. Chem. 1992, 57: 2747 - 84
Florio S.Granito C.Ingrosso G.Troisi L. Eur. J. Org. Chem. 2002, 3465 - 85
Cazes B.Julia S. Synth. Commun. 1977, 7: 273 - 86
Doering WvE.LaFlamme PM. Tetrahedron 1958, 2: 75 - 87
Moore WR.Ward HR. J. Org. Chem. 1960, 25: 2073 - 88
Moore WR.Ward HR. J. Org. Chem. 1962, 27: 4179 - 89
Skatteböl L. Tetrahedron Lett. 1961, 2: 167 - 90
Skatteböl L. Acta Chem. Scand. 1963, 17: 1683 - 91
Logan TJ. Tetrahedron Lett. 1961, 2: 173 - 92
Molander GA.Cormier EP. J. Org. Chem. 2005, 70: 2622 - 93
Lahrech M.Hacini S.Parrain J.-L.Santelli M. Tetrahedron Lett. 1997, 38: 3395 - 94
Baird MS.Nizovtsev AV.Bolesov IG. Tetrahedron 2002, 58: 1581 - 95
Satoh T.Kurihara T.Fujita K. Tetrahedron 2001, 57: 5369 - 96
Satoh T.Gouda Y. Tetrahedron Lett. 2006, 47: 2835 - 97
Hoffmann HMR. Angew. Chem., Int. Ed. Engl. 1969, 8: 556 - 98
Mikami K.Shimizu M. Chem. Rev. 1992, 92: 1021 - 99
Dias LC. Curr. Org. Chem. 2000, 4: 305 - 100
Gill GB.Hj MS.Kirollos I.Kirollos S. J. Chem. Soc., Perkin Trans. 1 1992, 2355 - 101
Golubev AS.Sergeeva NN.Hennig L.Kolomiets AF.Burger K. Tetrahedron 2003, 59: 1389 - 102
Sturla SJ.Kabaoui NM.Buchwald SL. J. Am. Chem. Soc. 1999, 121: 1976 - 103
Mori H.Ikoma K.Isoe S.Kitaura K.Katsumura S. J. Org. Chem. 1998, 63: 8704 - 104
Mori H.Ikoma K.Masui Y.Isoe S. Tetrahedron Lett. 1996, 37: 7771 - 105
Mori H.Ikoma K.Katsumura S. Chem. Commun. 1997, 2243 - 106
Nakano M.Noriyuki Furuichi .Mori H.Katsumura S. Tetrahedron Lett. 2001, 42: 7307 - 107
Bestmann HJ.Hartung H. Chem. Ber. 1966, 99: 1198 - 108
Hamlet Z.Barker WD. Synthesis 1970, 543 - 109
Oppolzer W.Chapuis C. Tetrahedron Lett. 1983, 24: 4665 - 110
Abell AD.Hoult DA.Morris KM.Taylor JM.Trent JO. J. Org. Chem. 1993, 58: 1531 - 111
Marshall JA.Wolf MA.Wallace EM. J. Org. Chem. 1997, 62: 367 - 112
Silveira CC.Boeck P.Braga AL. Tetrahedron Lett. 2000, 41: 1867 - 113
Ibrahim-Quali M.Sinibaladi M.-E.Troin Y.Gardette D.Gramain J.-C. Synth. Commun. 1997, 27: 1827 - 114
Lang RW.Hansen H.-J. Org. Synth. 1984, 62: 202 - 115
Lang RW.Hansen H.-J. Helv. Chim. Acta 1980, 63: 438 - 116
Lang RW.Kohl-Mines E.Hansen H.-J. Helv. Chim. Acta 1985, 68: 2249 - 117
Kang J.-E.Lee E.-S.Park S.-I.Shin S. Tetrahedron Lett. 2005, 46: 7431 - 118
Kumar K.Kaur S.Ishar MPS. Synlett 1999, 1237 - 119
Wittig G.Haag A. Chem. Ber. 1963, 96: 1535 - 120
Brummond KM.Chen D. Org. Lett. 2005, 7: 3473 - 121
Tömöskösi I.Bestmann HJ. Tetrahedron Lett. 1964, 5: 1293 - 122
Bestmann HJ.Tömösközi I. Tetrahedron 1968, 24: 3299 - 123
Melo TMVDPe.Cardoso AL.Gonsalves AMdAR.Storr RC.Pessoa JC.Paixã;o JA.Beja AM.Silva MR. Tetrahedron Lett. 2003, 44: 6409 - 124
Melo TMVDPe.Cardoso AL.Gonsalves AMdAR.Pessoa JC.Paixão JA.Beja AM. Eur. J. Org. Chem. 2004, 4830 - 125
Li C.-Y.Sun X.-L.Jing Q.Tang Y. Chem. Commun. 2006, 2980 - 126
Marszak MB.Simalty M.Seuleiman A. Tetrahedron Lett. 1974, 15: 1905 - 127
Fox DJ.Medlock JA.Vosser R.Warren S. J. Chem. Soc., Perkin Trans. 1 2001, 2240 - 128
Liu B.Wang KK.Petersen JL. J. Org. Chem. 1996, 61: 8503 - 129
Wang KK.Zhang H.-R.Petersen JL. J. Org. Chem. 1999, 64: 1650 - 130
Xi Z.Zhang W.-X.Song Z.Zheng W.Kong F.Takahashi T. J. Org. Chem. 2005, 70: 8785 - 131
Huang X.Xiong Z.-C. Tetrahedron Lett. 2003, 44: 5913 - 132
Huang X.Xiong Z.-C. Chem. Commun. 2003, 1714 - 133
Nagaoka Y.Tomioka K. J. Org. Chem. 1998, 63: 6428 - 134
Nagaoka Y.Inoue H.Tomioka K. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177: 1843 - 135
Wadsworth WS.Emmons WD. J. Am. Chem. Soc. 1961, 83: 1733 - 136
Fillion H.Hseine A.Péra M.-H. Synth. Commun. 1987, 929 - 137
Fillion H.Refouvelet B.Péra MH.Dufaud V. Synth. Commun. 1989, 19: 3343 - 138
Inoue H.Tsubouchi H.Nagaoka Y.Tomioka K. Tetrahedron 2002, 58: 83 - 139
Tanaka K.Otsubo K.Fuji K. Synlett 1995, 933 - 140
Tanaka K.Otsubo K.Fuji K. Tetrahedron Lett. 1995, 36: 9513 - 141
Tanaka K.Ostubo K.Fuji K. Tetrahedron Lett. 1996, 37: 3735 - 142
Yamazaki J.Watanabe T.Tanaka K. Tetrahedron: Asymmetry 2001, 12: 669 - 143
Tsubouchi A.Kira T.Takeda T. Synlett 2006, 2577 - 144
Crabbé P.André D.Fillion H. Tetrahedron Lett. 1979, 20: 893 - 145
Crabbé P.Fillion H.André D.Luche J.-L. J. Chem. Soc., Chem. Commun. 1979, 859 - 146
Searles S.Li Y.Nassim B.Lopes M.-TR.Tran PT.Crabbé P. J. Chem. Soc., Perkin Trans. 1 1984, 747 - 147
Crabbé P.Nassim B.Robert-Lopes M.-T. Org. Synth. 1985, 63: 203 - 148
Lee M.Ikeda I.Kawabe T.Mori S.Kanematsu K. J. Org. Chem. 1996, 61: 3406 - 149
Jayaprakash K.Venkatachalam CS.Balasubramanian KK. Tetrahedron Lett. 1999, 40: 6493 - 150
Bruyere D.Grigg R.Hinsley J.Hussain RK.Korn S.Cierva CODL.Sridharan V.Wang J. Tetrahedron Lett. 2003, 44: 8669 - 151
Ohno H.Takeoka Y.Kadoh Y.Miyamura K.Tanaka T. J. Org. Chem. 2004, 69: 4541 - 152
Chevliakov MV.Montgomery J. J. Am. Chem. Soc. 1999, 121: 11139 - 153
Grigg R.MacLachlan W.Rasparini M. Chem. Commun. 2000, 2241 - 154
Hayakawa K.Yasukouchi T.Kanematsu K. Tetrahedron Lett. 1987, 28: 5895 - 155
Yasukouchi T.Kanematsu K. Tetrahedron Lett. 1989, 30: 6559 - 156
Pattenden G.Robertson GM. Tetrahedron 1985, 41: 4001 - 157
Kang S.-K.Kim K.-J.Hong Y.-T. Angew. Chem. Int. Ed. 2002, 41: 1584 - 158
Kang S.-K.Baik T.-G.Kulak AN.Ha Y.-H.Lim Y.Park J. J. Am. Chem. Soc. 2000, 122: 11529 - 159
Dauvergne J.Burger A.Biellmann J.-F. Nucleosides, Nucleotides Nucleic Acids 2001, 20: 1775 - 160
Pyo S.Skowron JF.Cha J. Tetrahedron Lett. 1992, 33: 4703 - 161
Balakumar A.Janardanam S.Rajagoplan K. J. Org. Chem. 1993, 58: 5482 - 162
Bates RW.Satcharoen V. Synlett 2001, 532 - 163
Horváth A.Bäckvall J.-E. J. Org. Chem. 2001, 66: 8120 - 164
Ma S.Zhao S. J. Am. Chem. Soc. 2001, 123: 5578 - 165
Ma S.Hou H.Zhao S.Wang G. Synthesis 2002, 1643 - 166
Xu D.Li Z.Ma S. Tetrahedron Lett. 2003, 44: 6343 - 167
Souli C.Avlonitis N.Calogeropoulou T.Tsotinis A.Maksay G.Bíró T.Politi A.Mavromoustakos T.Makriyannis A.Reis H.Papadopoulos M. J. Med. Chem. 2005, 48: 5203 - 168
Kazmaier U.Lucas S.Klein M. J. Org. Chem. 2006, 71: 2429 - 169
Kezuka S.Kanemoto K.Takeuchi R. Tetrahedron Lett. 2004, 45: 6403 - 170
Shanmugam P.Rajagopalan K. Tetrahedron 1996, 52: 7737 - 171
Trost BM.Tour JM. J. Am. Chem. Soc. 1988, 110: 5231 - 172
Grigg R.Kilner C.Mariani E.Sridharan V. Synlett 2006, 3021 - 173
Casara P.Jund K.Bey P. Tetrahedron Lett. 1984, 25: 1891 - 174
Winkler JD.Ragains JR. Org. Lett. 2006, 8: 4031 - 175
Karstens WFJ.Rutjes FPJT.Hiemstra H. Tetrahedron Lett. 1997, 38: 6275 - 176
Beyersbergen van Henegouwen W.Hiemstra H. J. Org. Chem. 1997, 62: 8862 - 177
Mandal AK.Schneekloth JS.Crews CM. Org. Lett. 2005, 7: 3645 - 178
Trost BM.McClory A. Org. Lett. 2006, 8: 3627 - 179
Brummond KM.Dingess EA.Kent JL. J. Org. Chem. 1996, 61: 6096 - 180
Brummond KM.Wan H.Kent JL. J. Org. Chem. 1998, 63: 6535 - 181
Cunico RF.Kuan CP. J. Organomet. Chem. 1995, 487: 89 - 182
Satoh T.Itoh N.Watanabe S.Koike H.Matsuno H.Matsuda K.Yamakawa K. Tetrahedron 1995, 51: 9327 - 183
Satoh T.Hanaki N.Kuramochi Y.Inoue Y.Hosoya K.Sakai K. Tetrahedron 2002, 58: 2533 - 184
Satoh T.Sakamoto T.Watanabe M. Tetrahedron Lett. 2002, 43: 2043 - 185
Satoh T.Sakamoto T.Watanabe M.Tankano K. Chem. Pharm. Bull. 2003, 51: 966 - 186
Konoike T.Araki Y. Tetrahedron Lett. 1992, 33: 5093 - 187
Hailes HC.Isaac B.Javaid MH. Synth. Commun. 2003, 33: 29 - 188
McGrath MJ.Fletcher MT.König WA.Moore CJ.Cribb BW.Allsopp PG.Kitching W. J. Org. Chem. 2003, 68: 3739 - 189
Nativi C.Ricci A.Taddei M. Tetrahedron Lett. 1987, 28: 2751 - 190
Delouvrié B.Lacôte E.Fensterbank L.Malacria M. Tetrahedron Lett. 1999, 40: 3565 - 191
Mouriés V.Delouvrié B.Lacôte E.Fensterbank L.Malacria M. Eur. J. Org. Chem. 2002, 1776 - 192
Chan TH.Mychajlowskij W. Tetrahedron Lett. 1974, 15: 171 - 193
Chan TH.Mychajlowskij W.Ong BS.Harpp DN. J. Org. Chem. 1978, 43: 1526 - 194
Tius MA.Pal SK. Tetrahedron Lett. 2001, 42: 2605 - 195
Ohno H.Toda A.Oishi S.Tanaka T.Takemoto Y.Fujii N.Ibuka T. Tetrahedron Lett. 2000, 41: 5131 - 196
Ohno H.Miyamura K.Tanaka T.Ibuka T.Oishi S.Toda A.Takemoto Y.Fujii N.Ibuka T. J. Org. Chem. 2002, 67: 1359 - 197
Ohno H.Takeoka Y.Miyamura K.Kadoh Y.Tanaka T. Org. Lett. 2003, 5: 4763 - 198
Ohno H.Miyamura K.Mizutani T.Kadoh Y.Takeoka Y.Hamaguchi H.Tanaka T. Chem. Eur. J. 2005, 11: 3728 - 199
Ohno H.Kadoh Y.Fujii N.Tanaka T. Org. Lett. 2006, 8: 947 - 200
Ogasawara M.Hayashi T. Transition Metal-Catalyzed Synthesis of Allenes, In Modern Allene Chemistry Vol. 1:Krause N.Hashmi ASK. Wiley-VCH; Weinheim: 2004. p.93-140 - 201
Ogasawara M.Ikeda H.Hayashi T. Angew. Chem. Int. Ed. 2000, 39: 1042 - 202
Ogasawara M.Ikeda H.Nagano T.Hayashi T. J. Am. Chem. Soc. 2001, 123: 2089 - 203
Ogasawara M.Ikeda H.Nagano T.Hayashi T. Org. Lett. 2001, 3: 2615 - 204
Ogasawara M.Fan L.Ge Y.Takahashi T. Org. Lett. 2006, 8: 5409 - 205
Ogasawara M.Nagano T.Hayashi T. J. Org. Chem. 2005, 70: 5764 - 206
Han JW.Tokunaga N.Hayashi T. J. Am. Chem. Soc. 2001, 123: 12915 - 207
Matsumoto Y.Naito M.Hayashi T. Organometallics 1992, 11: 2732 - 208
Nakamura H.Kamakura T.Ishikura M.Biellmann J.-F. J. Am. Chem. Soc. 2004, 126: 5958 - 209
Nakamura H.Tashiro S.Kamakura T. Tetrahedron Lett. 2005, 46: 8333 - 210
Nakamura H.Onagi S.Kamukura T. J. Org. Chem. 2005, 70: 2357 - 211
Nakamura H.Kamakura T.Onagi S. Org. Lett. 2006, 8: 2095 - 212
Tsuji J.Mandai T. Angew. Chem., Int. Ed. Engl. 1995, 34: 2589 - 213
Tsuji J.Sugiura T.Minami I. Tetrahedron Lett. 1986, 27: 731 - 214
Piotti ME.Alper H. J. Org. Chem. 1997, 62: 8484 - 215
Molander GA.Sommers EM.Baker SR. J. Org. Chem. 2006, 71: 1563 - 216
Riveiros R.Rodríguez D.Sestelo JP.Sarandeses LA. Org. Lett. 2006, 8: 1403 - 217
Lee K.Seomoon D.Lee PH. Angew. Chem. Int. Ed. 2002, 41: 3901 - 218
Isaac MB.Chan T.-H. J. Chem. Soc., Chem. Commun. 1995, 1003 - 219
Wang Z.Hammond GB. J. Org. Chem. 2000, 65: 6547 - 220
Shen Q.Hammond GB. Org. Lett. 2001, 3: 2213 - 221
Miura T.Kiyota K.Kusama H.Lee K.Kim H.Kim S.Lee PH.Iwasawa N. Org. Lett. 2003, 5: 1725 - 222
Molander GA.Sommers EM. Tetrahedron Lett. 2005, 46: 2345 - 223
Takai K.Kokumai R.Toshikawa S. Synlett 2002, 1164 - 224
Ahmed M.Arnauld T.Barrett AGM.Braddock DC.Flack K.Procopiou PA. Org. Lett. 2000, 2: 551 - 225
Banerjee M.Roy S. Org. Lett. 2004, 6: 2137 - 226
Hayashi T.Tokunaga N.Inoue K. Org. Lett. 2004, 6: 305 - 227
Varghese JP.Knochel P.Marek I. Org. Lett. 2000, 2: 2849 - 228
Buchwald SL.Grubbs RH. J. Am. Chem. Soc. 1983, 105: 5490 - 229
Petasis NA.Hu Y.-H. J. Org. Chem. 1997, 62: 782 - 230
Hamada T.Mizojiri R.Urabe H.Sato F. J. Am. Chem. Soc. 2000, 122: 7138 - 231
Trost BM.Stiles DT. Org. Lett. 2005, 7: 2117 - 232
Shen L.Hsung RP.Zhang Y.Antoline JE.Zhang X. Org. Lett. 2005, 7: 3081