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

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

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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)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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