Synthesis, Inhaltsverzeichnis REVIEW © Georg Thieme Verlag Stuttgart · New York 5-Endo-Trig Radical Cyclizations Hiroyuki Ishibashi*a, Tatsunori Satob, Masazumi Ikedab a Faculty of Pharmaceutical Sciences, Kanazawa University, Takara-machi, Kanazawa 920-0934, Japanb Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, JapanFax: +81(76)2344476; e-Mail: isibasi@mail.p.kanazawa-u.ac.jp; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract 5-Endo-trig ring-closure is recognized as a disfavored process. However, a number of examples of such a type of cyclization have recently been reported. This review focuses on studies of 5-endo-trig radical cyclizations that provide new syntheses of five-membered carbo- and heterocyclic compounds. 1 Introduction 2 Reactions onto C=C Bonds 2.1 4-Pentenyl Radicals 2.2 Carbamoylmethyl Radicals 2.2.1 Bu3SnH-Mediated Reductive Cyclizations of α-Halo Amides 2.2.2 Ni/HOAc-Mediated Reductive Cyclizations of α-Halo Amides 2.2.3 Cu(I)-Mediated Reductive Cyclizations of α-Halo Amides 2.2.4 Mn(III)-Mediated Oxidative Cyclizations 2.3 α-Amidoyl Radicals 2.4 Vinyl Radicals 2.5 Acyl Radicals 2.6 Silicon-Centered Radicals 2.7 Sulfur-Centered Radicals 3 Reactions onto Oxygen Atoms of C=O Bonds 4 Reactions onto Nitrogen Atoms of C=N Bonds 5 Miscellaneous 6 Conclusions Key words alkaloids - tributyltin hydride - cyclizations - 5-endo-trig - α-halo amides - manganese(III) acetate - radicals Volltext Referenzen References 1a Giese B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds Pergamon; New York: 1986. 1b Curran DP. Synthesis 1988, 417 1c Curran DP. Synthesis 1988, 489 1d Curran DP. Comprehensive Organic Synthesis Vol. 4: Trost BM. Fleming I. Pergamon; Oxford: 1991. p.715 1e Jasperse CP. Curran DP. Fevig TL. Chem. Rev. 1991, 91: 1237 1f Naito T. Heterocycles 1999, 50: 505 1g Bowman WR. Cloonan MO. Krintel SL. J. Chem. Soc., Perkin Trans. 1 2001, 2885 2 Reversibility of cyclization of 4-pentenyl radicals has frequently been discussed. See: Ishibashi H. Kameoka C. Iriyama H. Kodama K. Sato T. Ikeda M. J. Org. Chem. 1995, 60: 1276 ; and references cited therein 3a Baldwin JE. J. Chem. Soc., Chem. Commun. 1976, 734 3b Baldwin JE. J. Chem. Soc., Chem. Commun. 1976, 736 4 Walling C. Pearson MS. J. Am. Chem. Soc. 1964, 86: 2262 5 »ekoviĘ Ž. Tetrahedron Lett. 1972, 749 6 Castaing M. Pereyre M. Ratier M. Blum PM. Davies AG. J. Chem. Soc., Perkin Trans. 2 1979, 287 7 Julia M. Le Goffic F. Bull. Soc. Chim. Fr. 1965, 1550 8 Curran DP. Chang C.-T. J. Org. Chem. 1989, 54: 3140 9 Pines H. Sih NC. Rosenfield DB. J. Org. Chem. 1966, 31: 2255 10 Bradney MAM. Forbes AD. Wood J. J. Chem. Soc., Perkin Trans. 2 1973, 1655 11 Reimann H. Sarre OZ. Can. J. Chem. 1971, 49: 344 12 Scheffold R. Dike M. Dike S. Herold T. Walder L. J. Am. Chem. Soc. 1980, 102: 3642 13 Gao J. Rusling JF. J. Org. Chem. 1998, 63: 218 14 Ponaras AA. Zaim . Tetrahedron Lett. 1993, 34: 2879 15 Nonami Y. Baran J. Sosnicki J. Mayr H. Masuyama A. Nojima M. J. Org. Chem. 1999, 64: 4060 16a Gilbert BC. Parry DJ. J. Chem. Soc., Perkin Trans. 2 1986, 1345 16b Gilbert BC. Parry DJ. J. Chem. Soc., Perkin Trans. 2 1988, 875 17 Wilt JW. Maravetz LL. Zawadzki JF. J. Org. Chem. 1966, 31: 3018 18a Crich D. Yao Q. J. Chem. Soc., Chem. Commun. 1993, 1265 18b Crich D. Yao Q. Tetrahedron 1994, 43: 12305 19a Rama Rao AVR. Singh AK. Reddy KM. Ravikumar K. J. Chem. Soc., Perkin Trans. 1 1993, 3171 19b Rama Rao AV. Singh AK. Rao BV. Reddy KM. Tetrahedron Lett. 1993, 34: 2665 20 Schmalz H.-G. Siegel S. Bats JW. Angew. Chem., Int. Ed. Engl. 1995, 34: 2383 21a Bogen S. Malacria M. J. Am. Chem. Soc. 1996, 118: 3992 21b Bogen S. Gulea M. Fensterbank L. Malacria M. J. Org. Chem. 1999, 64: 4920 22 Bommezijn S. Martin CG. Kennedy AR. Lizos D. Murphy JA. Org. Lett. 2001, 3: 3405 23a Ishibashi H. Nakamura N. Sato T. Takeuchi M. Ikeda M. Tetrahedron Lett. 1991, 32: 1725 23b Sato T. Nakamura N. Ikeda K. Okada M. Ishibashi H. Ikeda M. J. Chem. Soc., Perkin Trans. 1 1992, 2399 24a Sato T. Machigashira N. Ishibashi H. Ikeda M. Heterocycles 1992, 33: 139 24b Sato T. Chono N. Ishibashi H. Ikeda M. J. Chem. Soc., Perkin Trans. 1 1995, 1115 25a Goodall K. Parsons AF. J. Chem. Soc., Perkin Trans. 1 1994, 3257 25b Goodall K. Parsons AF. Tetrahedron 1996, 52: 6739 26a Baker SR. Parsons AF. Pons J.-F. Wilson M. Tetrahedron Lett. 1998, 38: 7197 26b Baker SR. Burton KI. Parsons AF. Pons J.-F. Wilson M. J. Chem. Soc., Perkin Trans. 1 1999, 427 27 Baker SR. Parsons AF. Wilson M. Tetrahedron Lett. 1998, 38: 2815 28 Ishibashi H. Fuke Y. Yamashita T. Ikeda M. Tetrahedron: Asymmetry 1996, 7: 2531 29 Ikeda M. Ohtani S. Sato T. Ishibashi H. Synthesis 1998, 1803 30 Goodall K. Parsons AF. Tetrahedron Lett. 1997, 38: 491 31 Ikeda M. Ohtani S. Yamamoto T. Sato T. Ishibashi H. J. Chem. Soc., Perkin Trans. 1 1998, 1763 32a Ishibashi H. Higuchi M. Ohba M. Ikeda M. Tetrahedron Lett. 1998, 39: 75 32b Ishibashi H. Kodama K. Higuchi M. Muraoka O. Tanabe G. Takeda Y. Tetrahedron 2001, 57: 7629 33 Fremont SL. Belletire JL. Ho DM. Tetrahedron Lett. 1991, 32: 2335 34 Belletire JL. Hagedorn CE. Ho DM. Krause J. Tetrahedron Lett. 1993, 34: 797 35a Ishibashi H. Matsukida H. Toyao A. Tamura O. Takeda Y. Synlett 2000, 1497 35b Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. submitted for publication. 36a Ikeda M. Hamada M. Yamashita T. Ikegami F. Sato T. Ishibashi H. Synlett 1998, 1246 36b Ikeda M. Hamada M. Yamashita T. Matsui K. Sato T. Ishibashi H. J. Chem. Soc., Perkin Trans. 1 1999, 1949 37 Ikeda M. Ohtani S. Okada M. Minakuchi E. Sato T. Ishibashi H. Heterocycles 1998, 47: 181 38a Parsons AF. Williams DAJ. Tetrahedron 2000, 56: 7217 38b El Bialy SAA. Ohtani S. Sato T. Ikeda M. Heterocycles 2001, 54: 1021 39 Parsons AF. Williams DAJ. Tetrahedron 1998, 54: 13405 40a Quiclet-Sire B. Saunier J.-B. Zard SZ. Tetrahedron Lett. 1996, 37: 1397 40b Cassayre J. Quiclet-Sire B. Saunier J.-B. Zard SZ. Tetrahedron 1998, 54: 1029 41 Cassayre J. Dauge D. Zard SZ. Synlett 2000, 471 42 Cassayre J. Quiclet-Sire B. Saunier J.-B. Zard SZ. Tetrahedron Lett. 1998, 39: 8995 43 Cassayre J. Zard SZ. Synlett 1999, 501 44 Davies DT. Kapur N. Parsons AF. Tetrahedron Lett. 1999, 40: 8615 45 Clark AJ. Dell CP. Ellard JM. Hunt NA. McDonagh JP. Tetrahedron Lett. 1999, 40: 8619 46 Davies DT. Kapur N. Parsons AF. Tetrahedron Lett. 1998, 39: 4397 47 Ishibashi H. Toyao A. Takeda Y. Synlett 1999, 1468 48 Toyao A. Chikaoka S. Takeda Y. Tamura O. Muraoka O. Tanabe G. Ishibashi H. Tetrahedron Lett. 2001, 42: 1729 49 Miyagi Y. Maruyama K. Kurokawa M. Yoshii A. Chem. Lett. 1988, 51 50 Burnett DA. Choi J.-K. Hart DJ. Tsai Y.-M. J. Am. Chem. Soc. 1984, 106: 8201 51 Beckwith ALJ. Boate DR. Tetrahedron Lett. 1985, 26: 1761 52 Buynak JD. Rao MN. Pajouhesh H. Chandrasekaran RY. Finn K. de Meester P. Chu SC. J. Org. Chem. 1985, 50: 4245 53 Gribble GW. Fraser HL. Badenock JC. Chem. Commun. 2001, 805 54a Ishibashi H. Ishita A. Tamura O. Tetrahedron Lett. 2002, 43: 473 54b Unpublished result. 55a Gimisis T. Chatgilialoglu C. J. Org. Chem. 1996, 61: 1908 55b Chatgilialoglu C. Gimisis T. Spada GP. Chem.-Eur. J. 1999, 5: 2866 56a Kittaka A. Tanaka H. Yamada N. Miyasaka T. Tetrahedron Lett. 1996, 37 : 2801 56b Kittaka A. Asakura T. Kuze T. Tanaka H. Yamada N. Nakamura KT. Miyasaka T. J. Org. Chem. 1999, 64: 7081 57 Urabe H. Kuwajima I. Tetrahedron Lett. 1986, 27: 1355 58 Kiyooka S. Kaneko Y. Matsue H. Hamada M. Fujiyama R. J. Org. Chem. 1990, 55: 5562 59a Barton TJ. Revis A. J. Am. Chem. Soc. 1984, 106 : 3802 59b Chatgilialoglu C. Woynar H. Ingold KU. Davies AG. J. Chem. Soc., Perkin Trans. 2 1983, 555 59c Sarasa JP. Igual J. Poblet JM. J. Chem. Soc., Perkin Trans. 2 1986, 861 60a Clive DLJ. Cantin M. J. Chem. Soc., Chem. Commun. 1995, 319 60b Clive DLJ. Yang W. MacDonald AC. Wang Z. Cantin M. J. Org. Chem. 2001, 66: 1966 61a Clive DLJ. Yang W. Chem. Commun. 1996, 1605 61b Sannigrahi M. Mayhew DL. Clive DLJ. J. Org. Chem. 1999, 64: 2776 62 Cai Y. Roberts BP. J. Chem. Soc., Perkin Trans. 1 1998, 467 63 Jenny C. Wipf P. Heimgarter H. Helv. Chim. Acta 1989, 72: 838 64 Journet M. Rouillard A. Cai D. Larsen RD. J. Org. Chem. 1997, 62: 8630 65 Menapace LW. Kuivila HG. J. Am. Chem. Soc. 1964, 86: 3047 66a Suginome H. Liu CF. Furusaki A. Chem. Lett. 1984, 911 66b Suginome H. Liu CF. Seko S. Kobayashi K. Furusaki A. J. Org. Chem. 1988, 53: 5952 66c Kobayashi K. Suzuki M. Suginome H. J. Org. Chem. 1992, 57: 599 67 Kobayashi K. Itoh M. Suginome H. Tetrahedron Lett. 1987, 28: 3369 68a Kagan J. Tetrahedron Lett. 1966, 6097 68b Harrison DA. Schwartz RN. Kagan J. J. Am. Chem. Soc. 1970, 92: 5793 68c Pappas SP. Blackwell JE. Tetrahedron Lett. 1968, 3337 68d Cohen KF. Pinhey JT. Smith RJ. Tetrahedron Lett. 1968, 4729 68e Mendenhall GD. Protasiewicz JD. Brown CE. Ingold KU. Lusztyk J. J. Am. Chem. Soc. 1994, 116: 1718 69a Yamamoto Y. Ohno M. Eguchi S. J. Org. Chem. 1994, 59: 4707 69b Yamamoto Y. Ohno M. Eguchi S. J. Am. Chem. Soc. 1995, 117: 9653 69c Yamamoto Y. Ohno M. Eguchi S. J. Org. Chem. 1996, 61: 9264 70 Citterio A. Arnoldi A. Minisci F. J. Org. Chem. 1979, 44: 2674 71 Kraus GA. Landgrebe K. Tetrahedron Lett. 1984, 25: 3939 72 Fristad WE. Peterson JR. J. Org. Chem. 1985, 50: 10 73 Rynard CM. Thankachan C. Tidwell TT. J. Am. Chem. Soc. 1979, 101: 1196 74 Tanner DD. Rahimi PM. J. Org. Chem. 1979, 44: 1674 75a Bowman WR. Stephenson PT. Terrett NK. Young AR. Tetrahedron Lett. 1994, 35: 6369 75b Bowman WR. Stephenson PT. Terrett NK. Young AR. Tetrahedron 1995, 51: 7959 76 Capella L. Montevecchi PC. Navacchia ML. J. Org. Chem. 1996, 61: 6783 77 Gopalsamy A. Balasubramanian KK. J. Chem. Soc., Chem. Commun. 1988, 28 78 Orito K. Uchiito S. Satoh Y. Tatsuzawa T. Harada R. Tokuda M. Org. Lett. 2000, 2: 307 79 Kunka CPA. Warkentin J. Can. J. Chem. 1990, 68: 575
