Control of axial chirality in absence of transition metals based on arynes

Comptes Rendus Chimie - Tập 20 - Trang 682-692 - 2017
Frédéric R. Leroux1, Armen Panossian1, David Augros1
1Université de Strasbourg, CNRS, LCM UMR 7509, 67000 Strasbourg, France

Tài liệu tham khảo

Bringmann, 2005, Angew. Chem., Int. Ed., 44, 5384, 10.1002/anie.200462661 Wallace, 2006, Org. Biomol. Chem., 4, 3197, 10.1039/b608470m Kozlowski, 2009, Chem. Soc. Rev., 38, 3193, 10.1039/b821092f Bringmann, 2011, Chem. Rev., 111, 563, 10.1021/cr100155e Ma, 2015, Chem.—Eur. J., 21, 11644, 10.1002/chem.201500869 Wencel-Delord, 2015, Chem. Soc. Rev., 44, 3418, 10.1039/C5CS00012B Hassan, 2002, Chem. Rev., 102, 1359, 10.1021/cr000664r Alberico, 2007, Chem. Rev., 107, 174, 10.1021/cr0509760 Seregin, 2007, Chem. Soc. Rev., 36, 1173, 10.1039/b606984n Daugulis, 2009, Acc. Chem. Res., 42, 1074, 10.1021/ar9000058 Chen, 2009, Angew. Chem., Int. Ed., 48, 5094, 10.1002/anie.200806273 Ackermann, 2009, Angew. Chem., Int. Ed., 48, 9792, 10.1002/anie.200902996 Colby, 2010, Chem. Rev., 110, 624, 10.1021/cr900005n Lyons, 2010, Chem. Rev., 110, 1147, 10.1021/cr900184e Wencel-Delord, 2012, Angew. Chem., Int. Ed., 51, 2247, 10.1002/anie.201107842 Königsberger, 2003, Org. Process Res. Dev., 7, 733, 10.1021/op034072x Pink, 2008, Org. Process Res. Dev., 12, 589, 10.1021/op800039g Huang, 2010, Org. Process Res. Dev., 14, 939, 10.1021/op100094p Toczko, 2012, 209 Magano, 2013, 313 Miyamoto, 2015, Org. Process Res. Dev., 19, 1054, 10.1021/acs.oprd.5b00161 Garcia-Lopez, 2016, Chem. Soc. Rev. Wittig, 1940, Ber. Dtsch. Chem. Ges., 73, 1193, 10.1002/cber.19400731113 Gilman, 1956, J. Am. Chem. Soc., 78, 2217, 10.1021/ja01591a053 Gilman, 1957, J. Org. Chem., 22, 447, 10.1021/jo01355a606 Dougherty, 1983, J. Org. Chem., 48, 5273, 10.1021/jo00174a023 Leroux, 2002, Angew. Chem., Int. Ed., 41, 4272, 10.1002/1521-3773(20021115)41:22<4272::AID-ANIE4272>3.0.CO;2-B Leroux, 2007, Adv. Synth. Catal., 349, 2705, 10.1002/adsc.200700211 Bonnafoux, 2010, Synlett, 2953 Diemer, 2011, Eur. J. Org. Chem., 341, 10.1002/ejoc.201001283 Bonnafoux, 2011, Chem.—Eur. J., 17, 11008, 10.1002/chem.201101529 Diemer, 2012, J. Org. Chem., 77, 6117, 10.1021/jo3009098 Leroux, 2012, Chem.—Eur. J., 18, 14232, 10.1002/chem.201202739 Oukhrib, 2014, Tetrahedron, 70, 1431, 10.1016/j.tet.2014.01.003 Berthelot-Bréhier, 2015, Org. Chem. Front., 2, 634, 10.1039/C5QO00067J Yalcouye, 2016, Eur. J. Org. Chem., 725, 10.1002/ejoc.201501503 Fer, 2016, Eur. J. Org. Chem., 4545, 10.1002/ejoc.201600727 Augros, 2016, Tetrahedron, 72, 5208, 10.1016/j.tet.2016.01.047 Zhang, 2015, Coord. Chem. Rev., 286, 1, 10.1016/j.ccr.2014.11.011 Loxq, 2016, Coord. Chem. Rev., 308, 131, 10.1016/j.ccr.2015.07.006 Demchuk, 2016, Phosphorus, Sulfur Silicon Relat. Elem., 191, 180, 10.1080/10426507.2015.1079197 F.R. Leroux, L. Bonnafoux, F. Colobert, WO 2008037440, LONZA AG. Leroux, 2004, 435 Leroux, 2006, Lett. Org. Chem., 3, 165, 10.2174/157017806779467979 Bonnafoux, 2011, Beilstein J. Org. Chem., 7, 1278, 10.3762/bjoc.7.148 Schlosser, 2005, Angew. Chem., Int. Ed., 44, 376, 10.1002/anie.200300645 Schlosser, 2013 Diemer, 2011, Eur. J. Org. Chem., 327, 10.1002/ejoc.201001217 Clayden, 2002, J. Am. Chem. Soc., 124, 5266, 10.1021/ja017702o Clayden, 2004, Tetrahedron, 60, 4387, 10.1016/j.tet.2004.01.099 Clayden, 2009, J. Am. Chem. Soc., 131, 5331, 10.1021/ja900722q 2002 Panossian, 2016, 813 Andersen, 1962, Tetrahedron Lett., 3, 93, 10.1016/S0040-4039(00)71106-3 Solladié, 1987, Synlett, 173 Mazzanti, 2006, J. Org. Chem., 71, 5474, 10.1021/jo060205b Ruzziconi, 2009, Chem.—Eur. J., 15, 2645, 10.1002/chem.200801963 Mazzanti, 2010, Chem.—Eur. J., 16, 9186, 10.1002/chem.200903372 Ruzziconi, 2010, Org. Biomol. Chem., 8, 4463, 10.1039/c0ob00136h Lunazzi, 2012, Org. Biomol. Chem., 10, 1847, 10.1039/c1ob06688a Furukawa, 1999, Top. Curr. Chem., 205, 89, 10.1007/3-540-48986-X_2 Knochel, 2007, Synlett, 2655, 10.1055/s-2007-991047 Lipshutz, 1994, Angew. Chem., Int. Ed., 33, 1842, 10.1002/anie.199418421 Lin, 1997, Tetrahedron Lett., 38, 1087, 10.1016/S0040-4039(96)02475-6 Guo-Qiang, 1997, Tetrahedron: Asymmetry, 8, 1369, 10.1016/S0957-4166(97)00117-1 Kyasnoor, 1998, Chem. Commun., 2713, 10.1039/a808146h Lipshutz, 1999, Tetrahedron Lett., 40, 3677, 10.1016/S0040-4039(99)00557-2 Meyers, 1978, Acc. Chem. Res., 11, 375, 10.1021/ar50130a002 Reuman, 1985, Tetrahedron, 41, 837, 10.1016/S0040-4020(01)96401-4 Gant, 1994, Tetrahedron, 50, 2297, 10.1016/S0040-4020(01)86953-2 Meyers, 2005, J. Org. Chem., 70, 6137, 10.1021/jo050470h Mortier, 2011, Curr. Org. Chem., 15, 2413, 10.2174/138527211796150561 Jantzi, 2006, Organometallics, 25, 5390, 10.1021/om060551j D. Augros, B. Yalcouye, S. Choppin, M. Chessé, A. Panossian, F. R. Leroux, accepted; http://dx.doi.org/10.1002/ejoc.201601239.