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Abstract
Following the success of the first intermolecular cyclopropanations of diazo acetoxy acetone with olefins using a novel p-nitro-Ru(II)-diphenyl-Pheox catalyst, other α-functionalized diazoketones have synthesized using the same reaction conditions. Consequently, chiral cyclopropyl products were formed with excellent yield (up to 87% yield), high diastereoselectivity (up to 99:1), and high enantioselectivity (up to 90% ee).
Keywords: Asymmetric synthesis, cyclopropanation, Ru(II)-pheox, diazoketones, p-nitro-Ru(II)-diphenyl-Pheox, carbene transfer.
[http://dx.doi.org/10.1016/S0040-4020(01)00777-3];
b) J. Chem. Rev., 2003, 103, 1051-1070.;
c) Wessjohann, L.A.; Brandt, W.; Thiemann, T. Chem. Rev., 2003, 103(4), 1625-1648.
[http://dx.doi.org/10.1021/cr0100188] [PMID: 12683792];
d) Lebal, H.; Marcoux, J-F.; Molinaro, C.; Charette, A.B. J. Chem. Rev., 2003, 103, 977-1050.
[http://dx.doi.org/10.1021/cr010007e];
e) Reichelt, A.; Martin, S.F. Acc. Chem. Res., 2006, 39(7), 433-442.
[http://dx.doi.org/10.1021/ar030255s] [PMID: 16846207];
f) Brackmann, F.; de Meijere, A. Chem. Rev., 2007, 107(11), 4493-4537.
[http://dx.doi.org/10.1021/cr078376j] [PMID: 17944521];
g) Chen, D.Y.K.; Pouwer, R.H.; Richard, J.A. Chem. Soc. Rev., 2012, 41(13), 4631-4642.
[http://dx.doi.org/10.1039/c2cs35067j] [PMID: 22592592];
h) Talele, T.T. J. Med. Chem., 2016, 59(19), 8712-8756.
[http://dx.doi.org/10.1021/acs.jmedchem.6b00472] [PMID: 27299736]
[http://dx.doi.org/10.1039/B701549F] [PMID: 17464409];
b) Lowenthal, R.E.; Abiko, A.; Masamune, S. Tetrahedron Lett., 1990, 31(42), 6005-6008.
[http://dx.doi.org/10.1016/S0040-4039(00)98014-6];
c) Evans, D.A.; Woerpel, K.A.; Hinman, M.M.; Faul, M.M. J. Am. Chem. Soc., 1991, 113(2), 726-728.
[http://dx.doi.org/10.1021/ja00002a080];
d) Itagaki, M.; Yamamoto, Y. Tetrahedron Lett., 2006, 47(4), 523-525.
[http://dx.doi.org/10.1016/j.tetlet.2005.11.086];
e) Rosenberg, M.L.; Krivokapic, A.; Tilset, M. Org. Lett., 2009, 11(3), 547-550.
[http://dx.doi.org/10.1021/ol802591j] [PMID: 19108673];
f) Doyle, M.P.; Brandes, B.D.; Kazala, A.P.; Pieters, R.J.; Jarstfer, M.B.; Watkins, L.M.; Eagle, C.T. Tetrahedron Lett., 1990, 31(46), 6613-6616.
[http://dx.doi.org/10.1016/S0040-4039(00)97128-4];
g) Doyle, M.P.; Pieters, R.J.; Martin, S.F.; Austin, R.E.; Oalmann, C.J.; Mueller, P. J. Am. Chem. Soc., 1991, 113(4), 1423-1424.
[http://dx.doi.org/10.1021/ja00004a059];
h) Ferrand, Y.; Le Maux, P.; Simonneaux, G. Org. Lett., 2004, 6(18), 3211-3214.
[http://dx.doi.org/10.1021/ol048567y] [PMID: 15330625];
i) Miller, J.A.; Jin, W.; Nguyen, S.T. Angew. Chem. Int. Ed., 2002, 41(16), 2953-2956.
[http://dx.doi.org/10.1002/1521-3773(20020816)41:16<2953::AIDANIE2953>3.0.CO;2-2];
j) Hoang, V.D.M.; Reddy, P.A.N.; Kim, T.J. Tetrahedron Lett., 2007, 48(45), 8014-8017.
[http://dx.doi.org/10.1016/j.tetlet.2007.09.035];
k) Chen, Y.; Zhang, X.P. J. Org. Chem., 2007, 72(15), 5931-5934.
[http://dx.doi.org/10.1021/jo070997p] [PMID: 17590051];
l) Zhu, S.F.; Xu, X.; Perman, J.A.; Zhang, X.P. J. Am. Chem. Soc., 2010, 132, 12796-12799.;
m) Suematsu, H.; Kanchiku, S.; Uchida, T.; Katsuki, T. J. Am. Chem. Soc., 2008, 130, 10327-10337.
[http://dx.doi.org/10.1021/acs.accounts.6b00070] [PMID: 27648664]
[http://dx.doi.org/10.1021/ol5014944] [PMID: 24918864];
b) Chanthamath, S.; Takaki, S.; Shibatomi, K.; Iwasa, S. Angew. Chem., 2013, 125(22), 5930-5933.
[http://dx.doi.org/10.1002/ange.201300468]
[http://dx.doi.org/10.1002/adsc.201801077]
[http://dx.doi.org/10.1021/jacs.0c09504] [PMID: 33497207]
[http://dx.doi.org/10.1246/cl.1992.167];
b) Nagle, D.G.; Gerwick, W.H. Tetrahedron Lett., 1990, 31(21), 2995-2998.
[http://dx.doi.org/10.1016/S0040-4039(00)89007-3];
c) White, J.D.; Jensen, M.S. J. Am. Chem. Soc., 1993, 115(7), 2970-2971.
[http://dx.doi.org/10.1021/ja00060a053];
d) Rodríguez, A.D.; Shi, J.G. Org. Lett., 1999, 1(2), 337-340.
[http://dx.doi.org/10.1021/ol990660c] [PMID: 10822572]
[http://dx.doi.org/10.1517/13543780903119167] [PMID: 19604119]
[http://dx.doi.org/10.2165/1131209-000000000-00000] [PMID: 19655817]
[http://dx.doi.org/10.1016/j.tetlet.2008.01.129];
b) Nicolas, I.; Roisnel, T.; Maux, P.L.; Simonneaux, G. Tetrahedron Lett., 2009, 50(36), 5149-5151.
[http://dx.doi.org/10.1016/j.tetlet.2009.06.131];
c) Lindsay, V.N.G.; Nicolas, C.A.B. J. Am. Chem. Soc., 2011, 133, 8972-8981.
[http://dx.doi.org/10.1021/ja201237j];
d) Lindsay, V.N.G.; Lin, W.; Charette, A.B. J. Am. Chem. Soc., 2009, 131(45), 16383-16385.
[http://dx.doi.org/10.1021/ja9044955] [PMID: 19860407];
e) Bauta, W.; Dodd, J.; Bullington, J.; Gauthier, D.; Leo, G.; McDonnell, P. Tetrahedron Lett., 2000, 41(10), 1491-1494.
[http://dx.doi.org/10.1016/S0040-4039(00)00002-2]
[http://dx.doi.org/10.1039/c2cc32706f] [PMID: 22751332]
[http://dx.doi.org/10.1021/acs.joc.7b01042] [PMID: 28762735]
[http://dx.doi.org/10.1039/C7CC03754F] [PMID: 28627577]
[http://dx.doi.org/10.1021/jo101105g] [PMID: 20672806]
[http://dx.doi.org/10.1021/jo50009a007]
[http://dx.doi.org/10.1002/cctc.201000161]
[http://dx.doi.org/10.1248/cpb.34.3252] [PMID: 3791497]
[http://dx.doi.org/10.1039/C7CY01161J]
[http://dx.doi.org/10.1002/ejoc.201500926]
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