Direct asymmetric Michael addition of thioether-based aryl sulfanyl-propan-2-one to nitroalkenes catalyzed by a chiral amine-thiourea bifunctional organocatalyst.

Abstract:

:Although the organocatalytic direct asymmetric Michael reactions of carbonyl compounds to nitroalkenes have been investigated intensely, the Michael reaction of the thioether-based donors remains a rather undeveloped field. This work concerns the asymmetric Michael addition of aryl sulfanyl-propan-2-one to nitroalkenes with benzoic acid as an additive, and chiral amine-thiourea as a bifunctional organocatalyst. The reactions provided the highly functionalized chiral adducts with excellent enantioselectivities (up to 96% ee) and good yields. Moreover, the further transformed products exhibited excellent diastereoselectivity.

journal_name

Chirality

journal_title

Chirality

authors

Jiang X,Zhang B,Zhang Y,Lin L,Yan W,Wang R

doi

10.1002/chir.20689

subject

Has Abstract

pub_date

2010-07-01 00:00:00

pages

625-34

issue

7

eissn

0899-0042

issn

1520-636X

journal_volume

22

pub_type

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