A highly diastereoselective synthesis of isoindolinone-centered Meyers’ tetracyclic lactams. Application to the asymmetric synthesis of 3-alkylisoindolinones

Bishop, 2000, Nature, 407, 395, 10.1038/35030148 Fischer, 2004, Curr. Med. Chem., 11, 1563, 10.2174/0929867043365062 McGovern, 2003, J. Med. Chem., 46, 1478, 10.1021/jm020427b Hardcastle, 2005, Bioorg. Med. Chem. Lett., 15, 1515, 10.1016/j.bmcl.2004.12.061 Zhuang, 1998, J. Med. Chem., 41, 157, 10.1021/jm970296s De Clercq, 1995, J. Med. Chem., 38, 2491, 10.1021/jm00014a001 Hiraga, K.; Saji, Y. PCT Int. Appl. WO 8303410, 1984; Chem. Abstr. 1984, 100, 51451. Wang, 2011, Tetrahedron Lett., 52, 2984, 10.1016/j.tetlet.2011.03.143 Belliotti, 1998, Bioorg. Med. Chem. Lett., 8, 1499, 10.1016/S0960-894X(98)00252-2 Takahashi, 1996, Synlett, 353, 10.1055/s-1996-5438 Kavoussi, 2000, Int. J. Neuropsychopharmacol., 3 Oppolzer, 1990, Tetrahedron Lett., 31, 5015, 10.1016/S0040-4039(00)97793-1 Murphy, 1995, Tetrahedron Lett., 36, 9533, 10.1016/0040-4039(95)02040-3 McAlonan, 2002, J. Chem. Soc., Perkin Trans. 1, 69 Stuk, 2003, Org. Proc. Res. Dev., 7, 851, 10.1021/op034060b Chen, 2002, Chin. J. Chem., 20, 1149, 10.1002/cjoc.20020201105 Chen, 2004, Tetrahedron, 60, 1651, 10.1016/j.tet.2003.11.092 Ruan, 2004, Synth. Commun., 34, 853, 10.1081/SCC-120028358 Hunter, 2000, Tetrahedron Lett., 41, 3755, 10.1016/S0040-4039(00)00485-8 Kundu, 2000, Tetrahedron, 56, 4777, 10.1016/S0040-4020(00)00359-8 Epsztajn, 2000, Tetrahedron, 60, 4837, 10.1016/S0040-4020(00)00403-8 Hoarau, 2000, Synthesis, 655, 10.1055/s-2000-6385 Yoda, 2000, Tetrahedron Lett., 41, 1775, 10.1016/S0040-4039(00)00014-9 Luzzio, 1998, Tetrahedron Lett., 39, 2285, 10.1016/S0040-4039(98)00293-7 Comins, 2005, Tetrahedron Lett., 46, 5639, 10.1016/j.tetlet.2005.06.105 Chen, 2005, Tetrahedron, 61, 1335, 10.1016/j.tet.2004.10.109 Comins, 2005, Org. Lett., 7, 95, 10.1021/ol047824w Allin, 1997, Tetrahedron Lett., 38, 3627, 10.1016/S0040-4039(97)00686-2 Allin, 2000, J. Chem. Soc., Perkin Trans. 1, 1715, 10.1039/b001569p Allin, 1999, Tetrahedron Lett., 40, 141, 10.1016/S0040-4039(98)80041-5 Allin, 1999, Tetrahedron Lett., 40, 143, 10.1016/S0040-4039(98)80042-7 Pérard-Viret, 2002, Tetrahedron, 58, 5103, 10.1016/S0040-4020(02)00462-3 Deniau, 2008, Tetrahedron: Asymmetry, 19, 2735, 10.1016/j.tetasy.2008.11.021 Jiang, 2010, Tetrahedron, 66, 172, 10.1016/j.tet.2009.11.003 Yu, 2011, Eur. J. Org. Chem., 892, 10.1002/ejoc.201001408 Stajer, 2005, Curr. Org. Chem., 9, 1277, 10.2174/1385272054863952 Enders, 2001, Can. J. Chem., 79, 1528, 10.1139/v01-140 Clayden, 2005, Tetrahedron: Asymmetry, 16, 2235, 10.1016/j.tetasy.2005.05.042 Sun, 2008, Org. Lett., 10, 1259, 10.1021/ol8001514 Lamblin, 2008, Tetrahedron: Asymmetry, 19, 111, 10.1016/j.tetasy.2007.11.014 Grigg, 1990, Tetrahedron Lett., 31, 3075, 10.1016/S0040-4039(00)89029-2 Shen, 2005, Org. Lett., 7, 775, 10.1021/ol047572z Clayden, 2003, Tetrahedron Lett., 44, 3059, 10.1016/S0040-4039(03)00545-8 Allin, 1998, Tetrahedron Lett., 39, 4905, 10.1016/S0040-4039(98)00892-2 Deniau, 2003, Tetrahedron: Asymmetry, 14, 2253, 10.1016/S0957-4166(03)00409-9 Meyers, 1997, Chem. Commun., 1, 10.1039/a604443c Groaning, 2000, Tetrahedron, 56, 9843, 10.1016/S0040-4020(00)00926-1 Amat, 2002, Angew. Chem., Int. Ed., 41, 335, 10.1002/1521-3773(20020118)41:2<335::AID-ANIE335>3.0.CO;2-Y Amat, 2002, J. Org. Chem., 67, 5343, 10.1021/jo025894f Amat, 2003, J. Org. Chem., 68, 1919, 10.1021/jo0266083 Ennis, 1996, J. Org. Chem., 61, 5813, 10.1021/jo960185l Allin, 2002, J. Org. Chem., 67, 9464, 10.1021/jo0205661 Penhoat, 2005, Tetrahedron Lett., 46, 8385, 10.1016/j.tetlet.2005.09.154 Nair, 2007, Indian J. Heterocycl. Chem., 16, 227 Bousquet, 2006, Tetrahedron, 62, 706, 10.1016/j.tet.2005.10.017 Bahajaj, 2004, Tetrahedron, 60, 1247, 10.1016/j.tet.2003.10.127 Bahajaj, 2004, Tetrahedron, 60, 1235, 10.1016/j.tet.2003.10.128 Sikoraiová, 2002, Tetrahedron Lett., 43, 4747, 10.1016/S0040-4039(02)00910-3 Iwamoto, 2000, J. Org. Chem., 65, 7944, 10.1021/jo000977m Breytenbach, 2000, Bioorg. Med. Chem. Lett., 10, 1629, 10.1016/S0960-894X(00)00306-1 Cho, 1996, Chem. Commun., 2115, 10.1039/CC9960002115 Yamazaki, 1996, Tetrahedron Lett., 37, 6161, 10.1016/0040-4039(96)01337-8 Yamazaki, 1997, Tetrahedron Lett., 38, 4623, 10.1016/S0040-4039(97)00991-X Couture, 1998, Tetrahedron Lett., 39, 2319, 10.1016/S0040-4039(98)00136-1 Deniau, E.; Enders, D. unpublished results. Meyers, 1991, J. Org. Chem., 56, 2294, 10.1021/jo00007a011 Fernandez, 2002, Angew. Chem. Int. Ed., 41, 831, 10.1002/1521-3773(20020301)41:5<831::AID-ANIE831>3.0.CO;2-6