Synthesis of azepane and nojirimycin iminosugars: the Sharpless asymmetric epoxidation of d-glucose-derived allyl alcohol and highly regioselective epoxide ring opening using sodium azide

Chong, 1985, J. Org. Chem., 50, 1560, 10.1021/jo00209a048 Mc Garrigle, 2005, Chem Rev., 105, 1564, 10.1021/cr0306945 Mimoun, 1983, J. Am. Chem. Soc., 105, 3101, 10.1021/ja00348a025 Butterworth, 1996, Chem. Commun., 1859, 10.1039/cc9960001859 Dembitsky, 2003, Tetrahedron, 59, 4701, 10.1016/S0040-4020(03)00701-4 Mizuno, 2005, Coord. Chem. Rev., 249, 1944, 10.1016/j.ccr.2004.11.019 Padwa, 2006, Arkivoc, 44, 8369 Boruwa, 2004, Tetrahedron Lett., 45, 7355, 10.1016/j.tetlet.2004.07.157 Sabita, 2002, Org. Lett., 4, 343, 10.1021/ol016979q Maruoka, 1985, Chem. Lett., 599, 10.1246/cl.1985.599 Caron, 1985, J. Org. Chem., 50, 1557, 10.1021/jo00209a047 Caron, 1988, J. Org. Chem., 53, 5185, 10.1021/jo00256a063 Saito, 1989, Tetrahedron Lett., 30, 4153, 10.1016/S0040-4039(00)99346-8 Davis, 2003, J. Org. Chem., 68, 75, 10.1021/jo026506c Onaka, 1986, Chem. Lett., 1327, 10.1246/cl.1986.1327 Sasaki, 2003, Org. Lett., 5, 1789, 10.1021/ol034455f Hayakawa, 1999, Tetrahedron Lett., 40, 4589, 10.1016/S0040-4039(99)00798-4 Behrens, 1983, Aldrichim. Acta, 16, 67 Karanjule, 2006, J. Org. Chem., 71, 4667, 10.1021/jo0601617 Bande, 2007, Tetrahedron: Asymmetry, 18, 1176, 10.1016/j.tetasy.2007.05.012 Bande, 2009, Synlett, 1959 Bande, 2009, Tetrahedron Lett., 50, 6906, 10.1016/j.tetlet.2009.09.139 Mane, 2008, J. Org. Chem., 73, 3284, 10.1021/jo800044r Tilekar, 2003, Tetrahedron, 59, 1873, 10.1016/S0040-4020(03)00177-7 Dhavale, 2003, Tetrahedron Lett., 44, 7321, 10.1016/S0040-4039(03)01870-7 Markad, 2006, Org. Biomol. Chem., 4, 3675, 10.1039/b609000a Lohray, 1995, J. Org. Chem., 60, 5958, 10.1021/jo00123a037 Painter, 2000, J. Chem. Soc., Perkin Trans. 1, 1157, 10.1039/a908986a Moris-Varas, 1996, J. Am. Chem. Soc., 118, 7647, 10.1021/ja960975c Merrer, 1997, Bioorg. Med. Chem., 5, 519, 10.1016/S0968-0896(96)00266-0 Poitout, 1994, Tetrahedron Lett., 35, 3293, 10.1016/S0040-4039(00)76888-2 Armbruster, 2000, Tetrahedron Lett., 41, 5483, 10.1016/S0040-4039(00)00905-9 Herdeis, 1999, Tetrahedron: Asymmetry, 10, 4521, 10.1016/S0957-4166(99)00466-8 Lampe, 1994, J. Org. Chem., 59, 5147, 10.1021/jo00097a014 Joseph, 2002, Tetrahedron, 58, 6907, 10.1016/S0040-4020(02)00757-3 Assiego, 2004, Tetrahedron Lett., 45, 2611, 10.1016/j.tetlet.2004.01.144 Paulsen, 1967, Chem. Ber., 100, 512, 10.1002/cber.19671000217 Li, 2004, Org. Biomol. Chem., 2, 1492, 10.1039/B402542C Andreana, 2002, Tetrahedron Lett., 43, 6525, 10.1016/S0040-4039(02)01465-X Joseph, 2002, Tetrahedron, 58, 6907, 10.1016/S0040-4020(02)00757-3 Fuentes, 2002, Tetrahedron: Asymmetry, 13, 1743, 10.1016/S0957-4166(02)00377-4 Painter, 2004, Bioorg. Med. Chem., 12, 225, 10.1016/j.bmc.2003.10.003 Andersen, 2000, Carbohydr. Res., 326, 22, 10.1016/S0008-6215(00)00018-5 Gallos, 2001, Tetrahedron Lett., 42, 7497, 10.1016/S0040-4039(01)01587-8 Inouye, 1968, Tetrahedron, 24, 2125, 10.1016/0040-4020(68)88115-3 Aoyagi, 1991, J. Org. Chem., 56, 815, 10.1021/jo00002a057 Kajimoto, 1991, J. Am. Chem. Soc., 113, 6187, 10.1021/ja00016a039 Fairbanks, 1992, Tetrahedron, 48, 3365, 10.1016/0040-4020(92)85012-4 Grandel, 1997, Tetrahedron Lett., 38, 8009, 10.1016/S0040-4039(97)10176-9 Barili, 1997, Tetrahedron, 53, 3409 Xu, 1997, J. Chem. Soc., Perkin Trans. 1, 1, 741, 10.1039/a605128f Asano, 1998, J. Nat. Prod., 61, 625, 10.1021/np9705726 Uriel, 1999, Synlett, 5993 Godin, 2002, J. Org. Chem., 67, 6960, 10.1021/jo0203903 Bols, 2002, Chem. Rev., 102, 515, 10.1021/cr000433k Pino-Gonzalez, 2003, Tetrahedron Lett., 44, 8353, 10.1016/j.tetlet.2003.09.116 Singh, 2003, Tetrahedron Lett., 44, 2387, 10.1016/S0040-4039(03)00218-1 Ko, 2004, J. Org. Chem., 69, 112, 10.1021/jo035371n Hughes, 1994, J. Nat. Prod. Rep., 135, 10.1039/np9941100135 Zeigler, 2003, Angew. Chem., Int. Ed., 27, 716, 10.1002/anie.198807161 Iida, 1987, J. Org. Chem., 52, 3337, 10.1021/jo00391a031 Ayad, 2004, Curr. Org. Chem., 8, 1211, 10.2174/1385272043370005 Takahata, 2004, Tetrahedron, 60, 8199, 10.1016/j.tet.2004.06.112 Reddy, 2005, Angew. Chem., Int. Ed., 43, 1898 Boucheron, 2006, Tetrahedron Lett., 47, 3081, 10.1016/j.tetlet.2006.02.157 Roy, 2006, Synthesis, 6, 1035 Song, 2007, Tetrahedron Lett., 48, 3115, 10.1016/j.tetlet.2007.01.110 Zhou, 2008, Org. Lett., 10, 3777, 10.1021/ol8014495 Racine, 2009, J. Org. Chem., 74, 1766, 10.1021/jo802255t Humphries, 1986, Cancer Res., 46, 5215 Truscheit, 1981, Angew. Chem., 20, 744, 10.1002/anie.198107441 Furneaux, 1997, Tetrahedron, 53, 245, 10.1016/S0040-4020(96)00967-2 Karpas, 1988, Proc. Natl. Acad. Sci. USA, 85, 9229, 10.1073/pnas.85.23.9229 Walker, 1987, Proc. Natl. Acad. Sci. USA, 84, 8120, 10.1073/pnas.84.22.8120 Sunkara, 1987, Biochem, Biophys. Res. Commun., 148, 206, 10.1016/0006-291X(87)91096-5 Johnson, 2002, Bioorg. Med. Chem. Lett., 12, 237, 10.1016/S0960-894X(01)00719-3 Patil, 2001, J. Org. Chem., 66, 1065, 10.1021/jo0010476 Masamme, 1985, Angew. Chem., Int. Ed., 24, 1, 10.1002/anie.198500013 Dhavale, 2004, J. Org. Chem., 69, 4760, 10.1021/jo049509t Somfai, 2003, Tetrahedron, 59, 1293, 10.1016/S0040-4020(02)01660-5 Kato, 2005, J. Med. Chem., 48, 2036, 10.1021/jm0495881 Dhavale, 2005, J. Org. Biomol. Chem., 3, 3720, 10.1039/b509216g