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. 2018 Dec 12;8(73):41699-41704.
doi: 10.1039/c8ra07809b.

Enantioselective Michael addition of malonates to α,β-unsaturated ketones catalyzed by 1,2-diphenylethanediamine

Wei Wang  1 , Ling Ye  2 , Zhichuan Shi  1 , Zhigang Zhao  1 , Xuefeng Li  1
Affiliations

Enantioselective Michael addition of malonates to α,β-unsaturated ketones catalyzed by 1,2-diphenylethanediamine

Wei Wang et al. RSC Adv. .

Abstract

A general and highly enantioselective Michael addition of malonates to cinnamones and chalcones has been developed. The commercially available 1,2-diphenylethanediamine could be directly utilized as the organocatalyst to furnish the desired adducts in satisfactory yield (61-99%) and moderate to excellent enantiopurity (65 to >99% ee). β-Ketoester was also a competent donor and was employed to construct densely functionalized cyclohexenones via a tandem Michael-aldol condensation process.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Synthetic transformation of adduct 5a.
Scheme 2
Scheme 2. Proposed reaction pathway.
See this image and copyright information in PMC

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