Direct Asymmetric Michael Reaction of α,β‐Unsaturated Aldehydes and Ketones Catalyzed by Two Secondary Amine Catalysts

Publisher： John Wiley & Sons Inc

E-ISSN： 1521-3757|130|7|1976-1980

ISSN： 0044-8249

Source： ANGEWANDTE CHEMIE, Vol.130, Iss.7, 2018-02, pp. : 1976-1980

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Abstract

AbstractA direct asymmetric Michael reaction of α,β‐unsaturated aldehydes and ketones proceeded in the presence of two pyrrolidine‐type catalysts, a diphenylprolinol silyl ether and hydroxyproline, to afford synthetically useful δ‐keto aldehydes with excellent diastereo‐ and enantioselectivity. Although there are several iminium ions and enamines in the reaction mixture, the iminium ion generated by the former catalyst reacts preferentially with the enamine generated by the latter catalyst.

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