Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co2-Schiff Base Complex

doi:10.3390/molecules15010532

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Molecules 2010, 15(1), 532-544; doi:10.3390/molecules15010532

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Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co₂-Schiff Base Complex

Makoto Furutachi, Zhihua Chen, Shigeki Matsunaga* and Masakatsu Shibasaki*

Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

* Authors to whom correspondence should be addressed.

Received: 24 December 2009; in revised form: 18 January 2010 / Accepted: 21 January 2010 / Published: 22 January 2010

(This article belongs to the Special Issue Bifunctional Catalysis)

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Abstract: Catalytic asymmetric 1,4-addition of β-keto esters to nitroalkenes is described. 2.5 mol % of a homobimetallic Lewis acid/Brønsted base bifunctional Co₂-Schiff base complex smoothly promoted the reaction in excellent yield (up to 99%), diastereoselectivity, and enantioselectivity (up to >30:1 dr and 98% ee). Catalyst loading was successfully reduced to 0.1 mol %. Mechanistic studies suggested that intramolecular cooperative functions of the two Co-metal centers are important for high catalytic activity and stereoselectivity.

Keywords: asymmetric catalysis; asymmetric synthesis; bifunctional catalyst; Michael reaction; Schiff base

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MDPI and ACS Style

Furutachi, M.; Chen, Z.; Matsunaga, S.; Shibasaki, M. Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co₂-Schiff Base Complex. Molecules 2010, 15, 532-544.

AMA Style

Furutachi M, Chen Z, Matsunaga S, Shibasaki M. Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co₂-Schiff Base Complex. Molecules. 2010; 15(1):532-544.

Chicago/Turabian Style

Furutachi, Makoto; Chen, Zhihua; Matsunaga, Shigeki; Shibasaki, Masakatsu. 2010. "Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co₂-Schiff Base Complex." Molecules 15, no. 1: 532-544.

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