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Synlett 2015; 26(08): 1111-1115
DOI: 10.1055/s-0034-1380265
DOI: 10.1055/s-0034-1380265
letter
Enantioselective Michael Addition Catalyzed by an Optically Active 1-Chlorovinyl Cobalt(III) Complex
Authors
Further Information
Publication History
Received: 17 December 2014
Accepted after revision: 01 February 2015
Publication Date:
09 March 2015 (online)
Abstract
The optically active 1-chlorovinyl cobalt(III) complex was prepared from the ketoiminatocobalt(II) complex upon treatment with sodium borohydride in the presence of 1,1,1-trichloroethane. The obtained complex was found to catalyze the enantioselective Michael addition of various malonates on cyclic or acyclic enones to afford the corresponding adduct. In this reaction, the use of sodium alkoxide as a base with 1-chlorovinyl cobalt(III) complex catalyst was crucial to improving both the reactivity and enantioselectivity.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380265.
- Supporting Information (PDF)
-
References and Notes
- 1 Nagata T, Yorozu K, Yamada T, Mukaiyama T. Angew. Chem., Int. Ed. Engl. 1995; 34: 2145
- 2 Yamada T, Nagata T, Sugi KD, Yorozu K, Ikeno T, Ohtsuka Y, Miyazaki D, Mukaiyama T. Chem. Eur. J. 2003; 9: 4485
- 3a Iwakura I, Hatanaka M, Kokura A, Teraoka H, Ikeno T, Nagata T, Yamada T. Chem. Asian J. 2006; 1: 656
- 3b Kokura A, Tanaka S, Teraoka H, Shibahara A, Ikeno T, Nagata T, Yamada T. Chem. Lett. 2007; 36: 26
- 4 Tsubo T, Chen H.-H, Yokomori M, Fukui K, Kikuchi S, Yamada T. Chem. Lett. 2012; 41: 780
- 5 Tsubo T, Yokomori M, Chen H.-H, Komori-Orisaku K, Kikuchi S, Koide Y, Yamada T. Chem. Lett. 2012; 41: 783
- 6 Tsubo T, Chen H.-H, Yokomori M, Kikuchi S, Yamada T. Bull. Chem. Soc. Jpn. 2013; 86: 983
- 7a Sasai H, Arai T, Shibasaki M. J. Am. Chem. Soc. 1994; 116: 1571
- 7b Sasai H, Arai T, Satow Y, Houk KN, Shibasaki M. J. Am. Chem. Soc. 1995; 117: 6194
- 7c Arai T, Sasai H, Aoe K.-i, Okamura K, Date T, Shibasaki M. Angew. Chem., Int. Ed. Engl. 1996; 35: 104
- 7d Arai T, Yamada YM. A, Yamamoto N, Sasai H, Shibasaki M. Chem. Eur. J. 1996; 2: 1368
- 7e Kim YS, Matsunaga S, Das J, Sekine A, Ohshima T, Shibasaki M. J. Am. Chem. Soc. 2000; 122: 6506
- 7f Matsunaga S, Ohshima T, Shibasaki M. Tetrahedron Lett. 2000; 41: 8473
- 7g Takita R, Ohshima T, Shibasaki M. Tetrahedron Lett. 2002; 43: 4661
- 7h Majima K, Takita R, Okada A, Ohshima T, Shibasaki M. J. Am. Chem. Soc. 2003; 125: 15837
- 8a DiMauro EF, Kozlowski MC. Org. Lett. 2001; 3: 1641
- 8b DiMauro EF, Kozlowski MC. Organometallics 2002; 21: 1454
- 8c Annamalai V, DiMauro EF, Carroll PJ, Kozlowski MC. J. Org. Chem. 2003; 68: 1973
- 9a Watanabe M, Murata K, Ikariya T. J. Am. Chem. Soc. 2003; 125: 7508
- 9b Dub PA, Wang H, Watanabe M, Gridnev ID, Ikariya T. Tetrahedron Lett. 2012; 53: 3452
- 9c Guo R, Chen X, Elpelt C, Song D, Morris RH. Org. Lett. 2005; 7: 1757
- 9d Clapham SE, Guo R, Zimmer-De Iuliis M, Rasool N, Lough A, Morris RH. Organometallics 2006; 25: 5477
- 9e Mahoney SJ, Dumas AM, Fillion E. Org. Lett. 2009; 11: 5346
- 10a Jha SC, Joshi NN. Tetrahedron: Asymmetry 2001; 12: 2463
- 10b Kumaraswamy G, Sastry MN. V, Jena N. Tetrahedron Lett. 2001; 42: 8515
- 10c Narasimhan S, Velmathi S, Balakumar R, Radhakrishnan V. Tetrahedron Lett. 2001; 42: 719
- 10d Velmathi S, Swarnalakshmi S, Narasimhan S. Tetrahedron: Asymmetry 2003; 14: 113
- 10e Jia Y.-X, Wu H, Liu R.-R. Synlett 2013; 25: 457
- 11a Kawara A, Taguchi T. Tetrahedron Lett. 1994; 35: 8805
- 11b Halland N, Aburel PS, Jørgensen KA. Angew. Chem. Int. Ed. 2003; 42: 661
- 11c Knudsen KR, Mitchell CE, Ley SV. Chem. Commun. 2006; 66
- 11d Wang J, Li H, Zu L, Jiang W, Xie H, Duan W, Wang W. J. Am. Chem. Soc. 2006; 128: 12652
- 11e Wascholowski V, Knudsen KR, Mitchell CE, Ley SV. Chem. Eur. J. 2008; 14: 6155
- 11f Yang YQ, Zhao G. Chem. Eur. J. 2008; 14: 10888
- 11g Adachi S, Tanaka F, Watanabe K, Harada T. Org. Lett. 2009; 11: 5206
- 11h Li P, Wen S, Yu F, Liu Q, Li W, Wang Y, Liang X, Ye J. Org. Lett. 2009; 11: 753
- 11i Li P, Wen S, Yu F, Liu Q, Li W, Wang Y, Liang X, Ye J. Org. Lett. 2009; 11: 753
- 11j Mao Z, Jia Y, Li W, Wang R. J. Org. Chem. 2010; 75: 7428
- 11k Mase N, Fukasawa M, Kitagawa N, Shibagaki F, Noshiro N, Takabe K. Synlett 2010; 2340
- 11l Procopio A, De Nino A, Nardi M, Oliverio M, Paonessa R, Pasceri R. Synlett 2010; 1849
- 11m Luo C, Jin Y, Du DM. Org. Biomol. Chem. 2012; 10: 4116
- 12a End N, Macko L, Zehnder M, Pfaltz A. Chem. Eur. J. 1998; 4: 818
- 12b Chen C, Zhu S.-F, Wu X.-Y, Zhou Q.-L. Tetrahedron: Asymmetry 2006; 17: 2761
- 12c Belokon’ YN, Maleev VI, Kataev DA, Saveleva TF, Skrupskaya TV, Nelyubina YV, North M. Tetrahedron: Asymmetry 2009; 20: 1746
- 13a Kobayashi T, Shimura T, Kurita Y, Katsumata Y, Kezuka S. Tetrahedron Lett. 2014; 55: 2818
- 13b Zhang Z, Liu X, Wang Z, Zhao X, Lin L, Feng X. Tetrahedron Lett. 2014; 55: 3797
- 14 Further examination of sodium salts are detailed in the Supporting Information.
- 15 Methyl and ethyl malonates did not react with 2-cyclohexen-1-one even at 0 °C.