Thioureas as Ligands in Organometallic Reactions

Dedicated to Professor K. C. Nicolaou on the occasion of his 68th birthday and Professor Henry N. C. Wong on the occasion of his 64^th birthday.

Abstract

Thioureas are air and moisture stable, and they can coordinate to various metal centers, making their derivatives versatile ligands for transition-metal-catalyzed reactions. This account provides an overview of recent developments in the use of thioureas as ligands in organometallic-catalyzed reactions, with particular emphasis on their application to the total synthesis of natural products.

1 Introduction

2 Development of Thioureas as Ligands in Transition-Metal-Catalyzed Reactions

2.1 Carbonylative Annulation

2.2 Pauson–Khand Reaction (Intramolecular and Intermolecular)

2.3 Thiourea–Palladium-Catalyzed Carbonylation of Terminal Olefins

2.4 Thiourea–Palladium-Catalyzed Heck Coupling Reaction

2.5 Suzuki Coupling and Suzuki Carbonylative Reaction

2.6 Negishi Coupling

2.7 Other Reactions

3 Applications in Total Synthesis of Natural Products

3.1 (±)-Schindilactone A

3.2 Crisamicin A

4 Conclusion and Outlook

Key words

thiourea - carbonylative annulation - transition metal - cobalt - palladium

• References

• 1a Bellina F, Rossi R. Chem. Rev. 2010; 110: 1082
• 1b Willis MC. Chem. Rev. 2010; 110: 725
• 1c Smith AM. R, Hii KK. Chem. Rev. 2011; 111: 1637
• 1d Xie J.-H, Zhu S.-F, Zhou Q.-L. Chem. Rev. 2011; 111: 1713
• 1e Weaver JD, Recio A, Grenning AJ, Tunge JA. Chem. Rev. 2011; 111: 1846
• 1f Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417
• 1g Liu C, Zhang H, Shi W, Lei A. Chem. Rev. 2011; 111: 1780
• 1h Magano J, Dunetz JR. Chem. Rev. 2011; 111: 2177
• 1i Aubert C, Fensterbank L, Garcia P, Malacria M, Simonneau A. Chem. Rev. 2011; 111: 1954
• 1j Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
• 1k Ackermann L. Chem. Rev. 2011; 111: 1315
• 1l Yamamoto Y. Chem. Rev. 2012; 112: 4736
• 2a Van der Boom ME, Milstein D. Chem. Rev. 2003; 103: 1759
• 2b Grushin VV. Chem. Rev. 2004; 104: 1629
• 2c Braunstein P. Chem. Rev. 2006; 106: 134
• 2d Fernández-Pérez H, Etayo P, Panossian A, Vidal-Ferran A. Chem. Rev. 2011; 111: 2119
• 3a Chelucci G, Thummel RP. Chem. Rev. 2002; 102: 3129
• 3b Kizirian J.-C. Chem. Rev. 2008; 108: 140
• 3c Hargaden GC, Guiry PJ. Chem. Rev. 2009; 109: 2505
• 4a Seebach D, Beck AK, Heckel A. Angew. Chem. Int. Ed. 2001; 40: 92
• 4b Brunel J.-M. Chem. Rev. 2005; 105: 857
• 5a Bayon JC, Claver C, Masdeu-Bulto AM. Coord. Chem. Rev. 1999; 193-195: 73
• 5b Masdeu-Bultü AM, Diéguez M, Martin E, Gümez M. Coord. Chem. Rev. 2003; 242: 159
• 5c Pellissier H. Tetrahedron 2007; 63: 1297
• 5d Mellah M, Voituriez A, Schulz E. Chem. Rev. 2007; 107: 5133
• 6 Liao Y, Hu Y, Wu J, Zhu Q, Donovan M, Fathi R, Yang Z. Curr. Med. Chem. 2003; 10: 2285
• 7a Nan Y, Miao H, Yang Z. Org. Lett. 2000; 2: 297
• 7b Miao H, Yang Z. Org. Lett. 2000; 2: 1765
• 8a Hosakawa T, Ueno T, Inui S, Murahashi S.-I. J. Am. Chem. Soc. 1981; 103: 2318
• 8b Backvall J.-E. Acc. Chem. Res. 1983; 16: 335
• 9a James DE, Hines LF, Stille JK. J. Am. Chem. Soc. 1976; 98: 1806
• 9b James DE, Stille JK. J. Am. Chem. Soc. 1976; 98: 1810
• 9c Drent E, Budzelaar PH. M. Chem. Rev. 1996; 96: 663
• 9d Reddy KR, Chen C.-L, Liu Y.-H, Peng S.-M, Chen J.-T, Liu S.-Y. Organometallics 1999; 18: 2574
• 10a Lloyd WG, Rowe DR. Environ. Sci. Technol. 1971; 5: 1133
• 10b Fenton DM, Steinwand PJ. J. Org. Chem. 1974; 39: 701
• 10c Tamaru Y, Yamada Y, Yamamoto Y, Yoshida Z.-I. Tetrahedron Lett. 1979; 20: 1401
• 10d Choudary BM, Prabhabar Reddy N, Lakshmi Kantam M. Tetrahedron Lett. 1985; 26: 6257
• 11a Nefkens SC. A, Sperrle M, Consiglio G. Angew. Chem., Int. Ed. Engl. 1993; 32: 1719
• 11b Hayashi M, Takezaki H, Hashimoto Y, Takaoki K, Saigo K. Tetrahedron Lett. 1998; 39: 7529
• 11c Takeuchi S, Ukaji Y, Inomata K. Bull. Chem. Soc. Jpn. 2001; 74: 955
• 12a Cauzzi D, Lanfranchi M, Marzolini G, Predieri G, Tiripicchio A, Costa M, Zanoni R. J. Organomet. Chem. 1995; 488: 115
• 12b Cauzzi D, Costa M, Gonsalvi L, Pellinghelli MA, Predieri G, Tiripiccio A, Zanoni R. J. Organomet. Chem. 1997; 541: 377
• 12c Sigman MS, Jacobsen EN. J. Am. Chem. Soc. 1998; 120: 4901
• 12d Zhang Y, Allen MJ. Tetrahedron Lett. 1999; 40: 5813
• 12e Jimenez Blanco JL, Benito JM, Mellet CO, Garcia Fernandez JM. Org. Lett. 1999; 1: 1217
• 12f Cauzzi D, Costa M, Cucci N, Graiff C, Grandi F, Predieri G, Tiripicchio A, Zanoni R. J. Organomet. Chem. 2000; 593: 431
• 12g Schreiner PR, Wittkopp A. Org. Lett. 2002; 4: 217
• 12h Wu F.-Y, Li Z, Wen Z.-C, Zhou N, Zhao Y.-F, Jiang Y.-B. Org. Lett. 2002; 4: 3203
• 12i Okino T, Hoashi Y, Takemoto T. Tetrahedron Lett. 2003; 44: 2817
• 13a Chiusoli GP, Venturello C, Merzoni S. Chem. Ind. (London) 1968; 977
• 13b Gabriele B, Salerno G, Costa MP, Chiusoli GP. J. Organomet. Chem. 1995; 503: 21
• 14a Touchard F, Fache F, Lemaire M. Tetrahedron: Asymmetry 1997; 8: 3319
• 14b Touchard F, Gamez P, Fache F, Lemaire M. Tetrahedron Lett. 1997; 38: 2275
• 14c Touchard F, Bernard M, Fache F, Delbecq F, Guiral V, Sautet P, Lemaire M. J. Organomet. Chem. 1998; 567: 133
• 14d Tommasino ML, Casalta M, Breuzard JA. J, Lemaire M. Tetrahedron: Asymmetry 2000; 11: 4835
• 14e Breuzard JA. J, Tommasino ML, Touchard F, Lemaire M, Bonnet MC. J. Mol. Catal. A: Chem. 2000; 156: 223
• 14f Touchard F, Bernard M, Fache F, Lemaire M. J. Mol. Catal. A: Chem. 1999; 140: 1
• 14g De Munno G, Gabriele B, Salerno G. Inorg. Chim. Acta 1995; 234
• 15 Kurnakow N. J. Prakt. Chem. 1894; 50: 481
• 16a Schafer M, Curran C. Inorg. Chem. 1966; 5: 265
• 16b Gosavi RK, Agarwaia U, Rao CN. R. J. Am. Chem. Soc. 1967; 89: 235
• 16c Gosavi RK, Rao CN. R. J. Inorg. Nucl. Chem. 1967; 29: 1937
• 16d O’Connor JE, Amma EL. Chem. Commun. 1968; 892
• 16e Cauzzi D, Costa M, Cucci N, Graiff C, Grandi F, Predieri G, Tiripicchio A, Zanoni R. J. Organomet. Chem. 2000; 431: 593
• 16f Cauzzi D, Lanfranchi M, Marzolini G, Predieri G, Tiripicchio A, Costa M, Zanoni R. J. Organomet. Chem. 1995; 488: 115
• 16g Cauzzi D, Costa M, Gonsalvi L, Pellinghelli MA, Predieri G, Tiripicchio A, Zanoni R. J. Organomet. Chem. 1997; 541: 377
• 17a Gruber-Woelfler H, Radaschitz PF, Feenstra PW, Hass W, Khinast JG. J. Catal. 2012; 286: 30
• 17b Hegedus LL, McCabe RW In Catalyst Poisoning . Marcel Dekker; New York: 1984
• 17c Hutton AT In Comprehensive Coordination Chemistry . Vol. 5. Wilkinson G, Gillard RD, McCleverty JA. Pergamon; Oxford: 1984: 1151
• 17d Kondo T, Mitsudo T.-A. Chem. Rev. 2000; 100: 3205
• 17e Dubois MR. Chem. Rev. 1989; 89: 1
• 18a Cagniant P, Carniant D. Adv. Hetercycl. Chem. 1975; 18: 337
• 18b Donnelly DM. X, Meegan MJ In Comprehensive Heterocyclic Chemistry . Vol. 4. Katritzky AR, Rees CW. Pergamon; Oxford: 1984: 657
• 19a Lütjens H, Scammells PJ. Synlett 1999; 1079
• 19b Kondo Y, Shiga F, Murata N, Sakamoto T, Yamanaka H. Tetrahedron 1994; 50: 11803
• 19c Colquhoun HM, Thompson DJ, Twigg MV. Carbonylation: Direct Synthesis of Carbonyl Compounds . Plenum Press; New York: 1991
• 19d Cort AD. Synth. Commun. 1990; 20: 757
• 20 The Flavonoids, Advances in Research since 1986 . Harborne JB. Chapman & Hall; London: 1993
• 21a Allan J, Robinson R. J. Chem. Soc. 1926; 2335
• 21b Robinson R, Venkataraman K. J. Chem. Soc. 1926; 2344
• 21c Lynch HM, O’Toole TM, Wheeler TS. J. Chem. Soc. 1952; 2063
• 21d Ollis WD, Weight D. J. Chem. Soc. 1952; 3826
• 21e Meyer-Dayan M, Bodo B, Deschamps-Vallet C, Molho D. Tetrahedron Lett. 1978; 19: 3359
• 21f Garcia H, Iborra S, Primo J, Miranda MA. J. Org. Chem. 1986; 51: 4432
• 21g McGarry LW, Detty MR. J. Org. Chem. 1990; 55: 4349
• 21h Pinto DC. G. A, Silva AM. S, Cavaleiro JA. S. J. Heterocycl. Chem. 1996; 33: 1887
• 21i Riva C, Toma CD, Donadel L, Boi C, Pennini R, Motta G, Leonardi A. Synthesis 1997; 195
• 21j Marder M, Viola H, Bacigaluppo JA, Colombo MI, Wasowski C, Wolfman C, Medina JH, Rúveda EA, Paladini AC. Biochem. Biophys. Res. Commun. 1998; 249: 481
• 21k Costantino L, Rastelli G, Gamberini MC, Vinson JA, Bose P, Iannone A, Staffieri M, Antolini L, Corso AD, Mura U, Albasini A. J. Med. Chem. 1999; 42: 1881
• 21l Dekermendjian K, Kahnberg P, Witt M.-R, Sterner O, Nielsen M, Liljefors T. J. Med. Chem. 1999; 42: 4343
• 21m Lokshin V, Heynderickx A, Samat A, Pèpe G, Guglielmetti R. Tetrahedron Lett. 1999; 40: 6761
• 21n Tabaka AC, Murthi KK, Pal K, Teleha CA. Org. Process Res. Dev. 1999; 3: 256
• 22a Khand IU, Knox GR, Pauson PL, Watts WE. J. Chem. Soc., Chem. Commun. 1971; 36
• 22b Khand IU, Knox GR, Pauson PL, Watts WE, Foreman MI. J. Chem. Soc., Perkin Trans. 1 1973; 977
• 22c Pauson PL, Khand IU. Ann. N. Y. Acad. Sci. 1977; 295: 2
• 23a Shambayati S, Crowe WE, Schreiber SL. Tetrahedron Lett. 1990; 31: 5289
• 23b Jeong N, Chung YK, Lee BY, Lee SH, Yoo S.-E. Synlett 1991; 204
• 23c Grossman RB, Buchwald SL. J. Org. Chem. 1992; 57: 5803
• 23d Gordon AR, Johnstone C, Kerr WJ. Synlett 1996; 1083
• 23e Murakami M, Itami K, Ito Y. J. Am. Chem. Soc. 1997; 119: 2950
• 23f Sugihara T, Yamada M, Ban H, Yamaguchi M, Kaneko C. Angew. Chem., Int. Ed. Engl. 1997; 36: 2801
• 23g Morimoto T, Chatani N, Fukumoto Y, Murai S. J. Org. Chem. 1997; 62: 3762
• 23h Kondo T, Suzuki N, Okada T, Mitsudo T. J. Am. Chem. Soc. 1997; 119: 6187
• 23i Rajesh T, Periasamy M. Tetrahedron Lett. 1998; 39: 117
• 23j Koga Y, Kobayashi T, Narasaka K. Chem. Lett. 1998; 249
• 23k Ingate ST, Marco-Contelles J. Org. Prep. Proced. Int. 1998; 30: 121
• 23l Geis O, Schmalz H.-G. Angew. Chem. Int. Ed. 1998; 37: 911
• 23m Jeong N In Transition Metals in Organic Chemistry . Beller M, Bolm C. Wiley-VCH; Weinheim: 1998: 560
• 23n Buchwald SL, Hicks FA In Comprehensive Asymmetric Catalysis . Jacobsen EN, Pfaltz A, Yamamoto H. Springer; Berlin: 1999: 491
• 23o Chung YK. Coord. Chem. Rev. 1999; 188: 297
• 23p Jeong N, Sung BK, Choi YK. J. Am. Chem. Soc. 2000; 122: 6771
• 23q Shibata T, Takagi K. J. Am. Chem. Soc. 2000; 122: 9852
• 23r Fletcher AJ, Christie SD. R. J. Chem. Soc., Perkin Trans. 1 2000; 1657
• 23s Brummond KM, Kent JL. Tetrahedron 2000; 56: 3263
• 23t Gibson SE, Stevenazzi A. Angew. Chem. Int. Ed. 2003; 42: 1800
• 23u Urgoiti JB, Anorbe L, Serrano LP, Dominguez G, Castells LP. Chem. Soc. Rev. 2004; 33: 32
• 23v Boañga LV. R, Krafft ME. Tetrahedron 2004; 60: 9795
• 23w Gibson SE, Mainolfi N. Angew. Chem. Int. Ed. 2005; 44: 3022
• 23x Mukai C, Yashida T, Sorimachi M, Odani A. Org. Lett. 2006; 8: 83
• 24 Tang Y, Deng L, Zhang Y, Dong G, Chen J, Yang Z. Org. Lett. 2005; 7: 593
• 25 Hayashi M, Hashimoto Y, Yamamoto Y, Usuki J, Saigo K. Angew. Chem. Int. Ed. 2000; 39: 631
• 26a Loubinoux B, Fixari B, Brunet JJ, Caubere P. J. Organomet. Chem. 1978; 105: C22
• 26b Brunet JJ, Sidot C, Loubinoux B, Caubere P. J. Org. Chem. 1979; 44: 2199
• 26c Brunet JJ, Sidot C, Caubere P. J. Org. Chem. 1981; 46: 3147
• 26d Caubere P. Angew. Chem., Int. Ed. Engl. 1983; 22: 599

For some examples, see:
• 27a Khand IU, Pauson PL. J. Chem. Res. Miniprint 1977; 168
• 27b Krafft ME. J. Am. Chem. Soc. 1988; 110: 968
• 27c Devasagayaraj A, Periasamy M. Tetrahedron Lett. 1989; 30: 595
• 27d Chung V, Lee BY, Jeong N, Hudecek M, Pauson PL. Organometallics 1993; 12: 220
• 27e Periasamy M, Reddy MR, Devasagayaraj A. Tetrahedron 1994; 50: 6955
• 27f Sugihara T, Yamada M, Yamaguchi M, Nishizawa M. Synlett 1999; 771
• 27g Krafft V. Tetrahedron Lett. 1988; 29: 999
• 27h Krafft ME, Juliano CA, Scott IL, Wright C, McEachin MD. J. Am. Chem. Soc. 1991; 113: 1693
• 28a Devasagayaraj A, Achyutha Rao S, Periasamy M. J. Organomet. Chem. 1991; 403: 387
• 28b Rao ML. N, Periasamy M. Organometallics 1996; 15: 442
• 28c Rao ML. N, Periasamy M. J. Organomet. Chem. 1997; 532: 143
• 28d Lakshmi M, Rao N, Perisaray M. J. Organomet. Chem. 1997; 532: 143
• 28e Periasamy M, Rajesh ML. N. T. J. Organomet. Chem. 1998; 571: 183
• 28f Rajesh T, Periasamy M. Tetrahedron Lett. 1999; 40: 817
• 28g Rajesh T, Periasamy M. Organometallics 1999; 18: 5709
• 29 Wang Y, Xu L, Yu R, Chen J, Yang Z. Chem. Commun. 2012; 48: 8183
• 30a Hicks FA, Kablaoui NM, Buchwald SL. J. Am. Chem. Soc. 1996; 118: 9450
• 30b Hicks FA, Kablaoui NM, Buchwald SL. J. Am. Chem. Soc. 1999; 121: 5881
• 30c Zhang M, Buchwald SL. J. Org. Chem. 1996; 61: 4498
• 30d Morimoto T, Chatani N, Fukumoto Y, Murai S. J. Org. Chem. 1997; 62: 3762
• 30e Jeong N, Lee S, Sung BK. Organometallics 1998; 17: 3642
• 30f Kobayashi T, Koga Y, Narasaka K. J. Organomet. Chem. 2001; 624: 73
• 31a Loupy A, Tchoubar B. Salt Effects in Organic and Organometallic Chemistry. VCH; Weinheim: 1992
• 31b Vogl EM, Groger H, Shibasaki M. Angew. Chem. Int. Ed. 1999; 38: 1570
• 31c Fagnou K, Lautens M. Angew. Chem. Int. Ed. 2002; 41: 26
• 32a Zhang Z, Lu X, Xu Z, Zhang Q, Han X. Organometallics 2001; 20: 3724
• 32b Wang Z, Zhang Z, Lu X. Organometallics 2000; 19: 775
• 33 Hicks FA, Berk SC, Buckwald SL. J. Org. Chem. 1996; 61: 2713
• 34 Lan Y, Deng L, Liu J, Wang C, Wiest O, Yang Z, Wu Y.-D. J. Org. Chem. 2009; 74: 5049
• 35 Wu N, Deng L.-J, Liu L.-Z, Liu Q, Li C.-C, Yang Z. Chem. Asian J. 2013; 8: 65
• 36a Mukai C, Yoshida T, Sorimachi M, Odani A. Org. Lett. 2006; 8: 83
• 36b Pallerla MK, Fox JM. Org. Lett. 2007; 9: 5625
• 36c Itoh N, Iwata T, Sugihara H, Inagaki F, Mukai C. Chem. Eur. J. 2013; 19: 8665
• 37 Dai M, Liang B, Wang C, Chen J, Yang Z. Org. Lett. 2004; 6: 221
• 38a Feringa BL. Transition Metals for Organic Synthesis . Vol. 2. Beller M, Bolm C. Wiley-VCH; Weinheim: 1998: 307
• 38b Tsuji J. Palladium Reagents and Catalysts . Wiley; Chichester: 1995: 19
• 38c Lautens M, Klute W, Tam W. Chem. Rev. 1996; 96: 49
• 38d Tamaru Y, Hijo M, Yoshida Z.-I. J. Org. Chem. 1991; 56: 1099
• 38e Suzuki T, Uozumi Y, Shibasaki M. J. Chem. Soc., Chem. Commun. 1991; 1593
• 38f Ukaji Y, Miyamoto M, Mikuni M, Takeuchi S, Inomata K. Bull. Chem. Soc. Jpn. 1996; 69: 735
• 38g Ogawa A, Kawabe K, Kawakami J, Mihara M, Hirao T. Organometallics 1998; 17: 3111
• 38h Aoyagi S, Hasegawa Y, Hirashima S, Kibayashi C. Tetrahedron Lett. 1998; 39: 2149
• 38i Cao P, Zhang X. J. Am. Chem. Soc. 1999; 121: 7708
• 38j Kreimerman S, Ryu I, Minakata S, Komatsu M. Org. Lett. 2000; 2: 389
• 39 Dai M, Wang C, Dong G, Xiang J, Luo T, Liang B, Chen J, Yang Z. Eur. J. Org. Chem. 2003; 4346
• 40 Liang B, Liu J, Gao Y.-X, Wongkhan K, Shu D.-X, Lan Y, Li A, Batsanov AS, Howard JA. H, Marder TB, Chen J.-H, Yang Z. Organometallics 2007; 26: 4756
• 41 Gao Y.-X, Chang L, Shi H, Liang B, Wongkhan K, Chaiyaveij D, Batsanov AS, Marder TB, Li C.-C, Yang Z, Huang Y. Adv. Synth. Catal. 2010; 352: 1955
• 42 Kikukawa K, Nagira K, Wada F, Matsuda T. Tetrahedron 1981; 37: 37
• 43 Sengupta S, Bhattacharyya S. J. Chem. Soc., Perkin Trans. 1 1993; 1943
• 44 Dai M, Liang B, Wang C, You Z, Xiang J, Dong G, Chen J, Yang Z. Adv. Synth. Catal. 2004; 346: 1669
• 45 Yang D, Chen Y.-C, Zhu N.-Y. Org. Lett. 2004; 6: 1577
• 46 Wang H, Liu J, Deng Y, Min T, Yu G, Wu X, Yang Z, Lei A. Chem. Eur. J. 2009; 15: 1499
• 47 Liu J, Wang H, Zhang H, Wu X, Zhang H, Deng Y, Yang Z, Lei A. Chem. Eur. J. 2009; 15: 4437
• 48 Yang M, Yip K.-T, Pan J.-H, Chen Y.-C, Zhu N.-Y, Yang D. Synlett 2006; 3057
• 49 Wu Z.-S, Yang M, Li H.-L, Qi Y.-X. Synthesis 2008; 9: 1415
• 50 Liu Y, Li X, Lin G, Ziang Z, Xiang J, Zhao M, Chen J, Yang Z. J. Org. Chem. 2008; 73: 4625
• 51 Li Z, Gao Y, Jiao Z, Wu N, Wang DZ, Yang Z. Org. Lett. 2008; 10: 5163
• 52 Xiao Q, Wang W.-H, Liu G, Meng F.-K, Chen J.-H, Yang Z, Shi Z.-J. Chem. Eur. J. 2009; 15: 7292
• 53a Jamison TF, Shambayati S, Crowe WE, Schreiber SL. J. Am. Chem. Soc. 1994; 116: 5505
• 53b Jamison TF, Shambayati S, Crowe WE, Schreiber SL. J. Am. Chem. Soc. 1997; 119: 4353
• 53c Castro J, Sorensen H, Riera A, Morin C, Moyano A, Pericas MA, Greene AE. J. Am. Chem. Soc. 1990; 112: 9388
• 53d Brummond KM, Lu J.-L. J. Am. Chem. Soc. 1999; 121: 5087
• 53e Cassayre J, Zard SZ. J. Am. Chem. Soc. 1999; 121: 6072
• 53f Cassayre J, Gagosz F, Zard SZ. Angew. Chem. Int. Ed. 2002; 41: 1783
• 53g Min S.-J, Danishefsky SJ. Angew. Chem. Int. Ed. 2007; 46: 2199
• 53h Kozaka T, Miyakoshi N, Mukai C. J. Org. Chem. 2007; 72: 10147
• 53i Miller KA, Martin SF. Org. Lett. 2007; 9: 1113
• 53j Madu CE, Lovely CJ. Org. Lett. 2007; 9: 4697
• 53k Inagaki F, Kinebuchi M, Miyakoshi N, Mukai C. Org. Lett. 2010; 12: 1800
• 53l Nakayama A, Kogure N, Kitajima M, Takayama H. Angew. Chem. Int. Ed. 2011; 50: 8025
• 53m Yang Y, Fu X.-N, Chen J.-W, Zhai H.-B. Angew. Chem. Int. Ed. 2012; 51: 9825
• 53n Fujioka K, Yokoe H, Yoshida M, Shishido K. Org. Lett. 2012; 14: 244
• 53o Liu Q, Yue G.-Z, Wu N, Lin G, Li Y.-Z, Quan JM, Li C.-C, Wang G.-X, Yang Z. Angew. Chem. Int. Ed. 2012; 51: 12072
• 53p Huang J, Fang L.-C, Long R, Shi L.-L, Shen H.-J, Li C.-C, Yang Z. Org. Lett. 2013; 15: 4018
• 53q Chen J, Gao P, Yu F, Yang Y, Zhu S, Zhai H. Angew. Chem. Int. Ed. 2012; 51: 5897
• 53r Hirose T, Miyakoshi N, Mukai C. J. Org. Chem. 2008; 73: 1061
• 53s Grillet F, Huang C.-F, Brummond KM. Org. Lett. 2011; 13: 6304
• 53t Hayashi Y, Miyakoshi N, Kitagaki S, Chisato Mukai C. Org. Lett. 2008; 10: 2385
• 53u Jørgensen L, McKerrall SJ, Kuttruff CA, Ungeheuer F, Felding J, Baran PS. Science (Washington, D.C.) 2013; 341: 878
• 54 Tang Y, Zhang Y, Dai M, Luo T, Deng L, Chen J, Yang Z. Org. Lett. 2005; 7: 885
• 55 Xiao Q, Ren W.-W, Chen Z.-X, Sun T.-W, Li Y, Ye Q.-D, Gong J.-X, Meng F.-K, You L, Liu Y.-F, Zhao M.-Z, Xu L.-M, Shan Z.-H, Shi Y, Tang Y.-F, Chen J.-H, Yang Z. Angew. Chem. Int. Ed. 2011; 50: 7373
• 56 Li Z, Gao Y, Tang Y, Dai M, Wang G, Wang Z, Yang Z. Org. Lett. 2008; 10: 3017