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

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

Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
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Received: 24 December 2009 / Revised: 18 January 2010 / Accepted: 21 January 2010 / Published: 22 January 2010
(This article belongs to the Special Issue Bifunctional Catalysis)

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 asymmetric catalysis; asymmetric synthesis; bifunctional catalyst; Michael reaction; Schiff base
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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