Nucleophilic addition of potassium organotrifluoroborates to chiral cyclic N-acyliminium ions: stereoselective synthesis of functionalized N-heterocycles

Tetrahedron - Tập 64 - Trang 3306-3314 - 2008
Adriano S. Vieira1, Fernando P. Ferreira2, Pedro F. Fiorante1, Rafael C. Guadagnin1, Hélio A. Stefani1,2,3
1Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, SP, Brazil
2Departamento de Biofisica, Universidade Federal de São Paulo, SP, Brazil
3Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brazil

Tài liệu tham khảo

For reviews of N-acyliminium ion chemistry, see: de Koning, 1995, Vol. E21, 1953 Speckamp, 2000, Tetrahedron, 56, 3817, 10.1016/S0040-4020(00)00159-9 Maryanoff, 2004, Chem. Rev., 104, 1431, 10.1021/cr0306182 See, for example: Pilli, 1995, J. Org. Chem., 60, 717, 10.1021/jo00108a040 Pilli, 1996, J. Org. Chem., 61, 3187, 10.1021/jo9513020 Dhimane, 1997, Tetrahedron Lett., 38, 1415, 10.1016/S0040-4039(97)00099-3 Batey, 2000, Tetrahedron Lett., 41, 9935, 10.1016/S0040-4039(00)01790-1 El-Nezhawy, 2002, Eur. J. Org. Chem., 4137, 10.1002/1099-0690(200212)2002:24<4137::AID-EJOC4137>3.0.CO;2-X Bennet, 2004, Tetrahedron, 60, 4491, 10.1016/j.tet.2004.01.100 Osante, 2004, Tetrahedron Lett., 45, 1253, 10.1016/j.tetlet.2003.11.122 Huang, 2003, Org. Lett., 5, 1927, 10.1021/ol034505g Meng, 2004, Tetrahedron: Asymmetry, 15, 3899, 10.1016/j.tetasy.2004.10.030 Chen, 2004, Tetrahedron, 60, 10223, 10.1016/j.tet.2004.09.001 Huang, 2006, Synlett, 1133, 10.1055/s-2006-941565 1998, Vol. 50 Zaugg, 1970, Synthesis, 49, 10.1055/s-1970-21579 Schmidt, 1973, Angew. Chem., 85, 235, 10.1002/ange.19730850602 1973, Angew. Chem., Int. Ed. Engl., 12, 212, 10.1002/anie.197302121 Kraus, 1982, J. Chem. Soc., Chem. Commun., 134, 10.1039/c39820000134 Thaning, 1986, Helv. Chim. Acta, 69, 1711, 10.1002/hlca.19860690727 Thaning, 1990, J. Org. Chem., 55, 1406, 10.1021/jo00291a065 Renaud, 1986, Helv. Chim. Acta, 69, 1704, 10.1002/hlca.19860690726 Arai, 1992, Chem. Pharm. Bull., 40, 1670, 10.1248/cpb.40.1670 Russowsky, 2000, Tetrahedron Lett., 41, 9939, 10.1016/S0040-4039(00)01828-1 Klitzke, 2001, Tetrahedron Lett., 42, 5605, 10.1016/S0040-4039(01)01084-X Andrade, 2005, J. Braz. Chem. Soc., 16, 535 Ben Othman, 2005, Org. Lett., 7, 2825, 10.1021/ol050576z Ben Othman, 2005, Org. Lett., 7, 5335, 10.1021/ol052357j Bernardi, 1990, Tetrahedron Lett., 31, 4949, 10.1016/S0040-4039(00)97777-3 Koot, 1991, Tetrahedron Lett., 31, 401, 10.1016/S0040-4039(00)92639-X Lennartz, 1999, Tetrahedron, 55, 14407, 10.1016/S0040-4020(99)00904-7 Huang, 2003, Synlett, 1663, 10.1055/s-2003-40988 Kano, 1988, J. Org. Chem., 53, 3865, 10.1021/jo00251a042 Onoue, 1979, Tetrahedron Lett., 20, 3867, 10.1016/S0040-4039(01)95546-7 Kise, 1994, Tetrahedron Lett., 35, 1561, 10.1016/S0040-4039(00)76758-X Rossi, 1995, J. Am. Chem. Soc., 117, 9604, 10.1021/ja00142a045 Yamada, 1989, Tetrahedron Lett., 30, 5611, 10.1016/S0040-4039(01)93812-2 Ludwig, 1990, Acta Chem. Scand., 44, 707, 10.3891/acta.chem.scand.44-0707 Wistrand, 1991, Tetrahedron, 47, 573, 10.1016/S0040-4020(01)87047-2 Collado, 1995, J. Org. Chem., 60, 5011, 10.1021/jo00121a020 Comins, 1988, Tetrahedron Lett., 29, 6711, 10.1016/S0040-4039(00)82435-1 Brown, 1991, Tetrahedron, 47, 1311, 10.1016/S0040-4020(01)86388-2 Shono, 1990, Tetrahedron Lett., 31, 6385, 10.1016/S0040-4039(00)97071-0 Hanson, 1989, Tetrahedron Lett., 30, 5751, 10.1016/S0040-4039(00)76188-0 Lundkvist, 1990, Tetrahedron Lett., 31, 719, 10.1016/S0040-4039(00)94612-4 Jacobi, 1997, J. Am. Chem. Soc., 119, 3409, 10.1021/ja9642727 Thaning, 1989, Acta Chem. Scand., 43, 290, 10.3891/acta.chem.scand.43-0290 Katoh, 1994, Tetrahedron, 50, 6221, 10.1016/S0040-4020(01)80643-8 Irie, 1985, J. Chem. Soc., Chem. Commun., 633, 10.1039/c39850000633 Oba, 2001, Tetrahedron Lett., 42, 5901, 10.1016/S0040-4039(01)01120-0 Oba, 2002, Tetrahedron, 58, 9359, 10.1016/S0040-4020(02)01218-8 Oba, 2004, Tetrahedron, 60, 8089, 10.1016/j.tet.2004.06.109 Oba, 2005, Synth. Commun., 35, 2966, 10.1080/00397910500278446 Shono, 1981, J. Am. Chem. Soc., 103, 1172, 10.1021/ja00395a029 Shono, 1984, J. Org. Chem., 49, 300, 10.1021/jo00176a016 Louwrier, 1996, Tetrahedron, 52, 2603, 10.1016/0040-4020(95)01085-8 Tranchant, 2006, Tetrahedron Lett., 47, 4477, 10.1016/j.tetlet.2006.04.090 Okitsu, 2001, J. Org. Chem., 66, 809, 10.1021/jo001297m Shono, 1981, Chem. Lett., 1121, 10.1246/cl.1981.1121 Martin, 1996, J. Am. Chem. Soc., 118, 3299, 10.1021/ja9542146 Germon, 1984, Synthesis, 40, 10.1055/s-1984-30725 Thaning, 1992, Acta Chem. Scand., 46, 194, 10.3891/acta.chem.scand.46-0194 McClure, 1995, J. Org. Chem., 60, 454, 10.1021/jo00107a028 Martin, 1996, Tetrahedron, 52, 7251, 10.1016/0040-4020(96)00249-9 Angst, 1987, Pure Appl. Chem., 59, 373, 10.1351/pac198759030373 Washburn, 2003, Org. Lett., 5, 3523, 10.1021/ol0354066 Batey, 1999, J. Am. Chem. Soc., 121, 5075, 10.1021/ja983801z Morgan, 2008, Tetrahedron, 64, 1409, 10.1016/j.tet.2007.11.046 Matteson, 1995 Pelter, 1988 Stefani, 2007, Tetrahedron, 63, 3623, 10.1016/j.tet.2007.01.061 Cella, 2006, J. Org. Chem., 71, 224, 10.1021/jo052061r Cella, 2006, Tetrahedron, 62, 5656, 10.1016/j.tet.2006.03.090 Stefani, 2005, Tetrahedron Lett., 46, 563, 10.1016/j.tetlet.2004.11.160 Cella, 2006, Tetrahedron Lett., 47, 5075, 10.1016/j.tetlet.2006.05.088 Cella, 2008, Tetrahedron Lett., 49, 16, 10.1016/j.tetlet.2007.11.031 Stefani, 2006, Z. Kristallogr., 221, 167 Caracelli, 2007, Z. Kristallogr., 222, 345 Petasis, 1993, Tetrahedron Lett., 34, 583, 10.1016/S0040-4039(00)61625-8 Petasis, 1997, J. Am. Chem. Soc., 119, 445, 10.1021/ja963178n Petasis, 1997, Tetrahedron, 53, 16463, 10.1016/S0040-4020(97)01028-4 Schlienger, 2000, Tetrahedron Lett., 41, 1303, 10.1016/S0040-4039(99)02273-X Li, 2004, Chem. Commun., 1382, 10.1039/b403759f Solin, 2005, Org. Lett., 7, 689, 10.1021/ol0475010 Wallner, 2006, Chem.—Eur. J., 12, 6976, 10.1002/chem.200600406 Kabalka, 2004, Tetrahedron Lett., 45, 729, 10.1016/j.tetlet.2003.11.049 Tremblay-Morin, 2004, Tetrahedron Lett., 45, 3471, 10.1016/j.tetlet.2004.03.014 Billard, 2002, J. Org. Chem., 67, 997, 10.1021/jo016265t Bir, 1988, J. Organomet. Chem., 340, 267, 10.1016/0022-328X(88)80020-2 Metten, 2006, Tetrahedron, 62, 6018, 10.1016/j.tet.2006.04.005 Cieplak, 1981, J. Am. Chem. Soc., 103, 4540, 10.1021/ja00405a041 Meyers, 1989, J. Org. Chem., 54, 2509, 10.1021/jo00272a007 Jeroncic, 1991, J. Org. Chem., 56, 387, 10.1021/jo00001a070 Danishefsky, 1989, J. Am. Chem. Soc., 111, 3456, 10.1021/ja00191a067 Frohn, 2000, J. Organomet. Chem., 598, 127, 10.1016/S0022-328X(99)00690-7 Molander, 2002, J. Org. Chem., 67, 8416, 10.1021/jo0262356