Enantioselective organocatalytic Michael Addition of ketones to alkylidene malonates

Siang En Syu; Chan Hui Huang; Ko Wei Chen; Chia Jui Lee; Utpal Das; Yeong Jiunn Jang; Wenwei Lin

doi:10.1002/chir.22055

Enantioselective organocatalytic Michael Addition of ketones to alkylidene malonates

Siang En Syu, Chan Hui Huang, Ko Wei Chen, Chia Jui Lee, Utpal Das, Yeong Jiunn Jang, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

Organocatalysts bearing sulfide or sulfone functions () were studied for the direct asymmetric Michael addition of ketones and alkylidene malonates. The organocatalyst (S)-2-((naphthalen-2-ylthio)methyl)pyrrolidine, bearing a pyrrolidine and a sulfide moiety, showed a very high catalytic activity in the absence of additives. The reaction condition is mild, and the Michael adducts were obtained in very good enantioselectivities (up to 96%), diastereoselectivities (up to >95:5), and chemical yields (up to 95%). Chirality 24:600-605, 2012. © 2012 Wiley Periodicals, Inc.

Original language	English
Pages (from-to)	600-605
Number of pages	6
Journal	Chirality
Volume	24
Issue number	8
DOIs	https://doi.org/10.1002/chir.22055
Publication status	Published - 2012 Aug

Keywords

Michael addition
alkylidene malonate
ketones
organocatalysis
stereoselectivity

ASJC Scopus subject areas

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

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10.1002/chir.22055

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title = "Enantioselective organocatalytic Michael Addition of ketones to alkylidene malonates",

abstract = "Organocatalysts bearing sulfide or sulfone functions () were studied for the direct asymmetric Michael addition of ketones and alkylidene malonates. The organocatalyst (S)-2-((naphthalen-2-ylthio)methyl)pyrrolidine, bearing a pyrrolidine and a sulfide moiety, showed a very high catalytic activity in the absence of additives. The reaction condition is mild, and the Michael adducts were obtained in very good enantioselectivities (up to 96%), diastereoselectivities (up to >95:5), and chemical yields (up to 95%). Chirality 24:600-605, 2012. {\textcopyright} 2012 Wiley Periodicals, Inc.",

keywords = "Michael addition, alkylidene malonate, ketones, organocatalysis, stereoselectivity",

author = "Syu, {Siang En} and Huang, {Chan Hui} and Chen, {Ko Wei} and Lee, {Chia Jui} and Utpal Das and Jang, {Yeong Jiunn} and Wenwei Lin",

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T1 - Enantioselective organocatalytic Michael Addition of ketones to alkylidene malonates

AU - Syu, Siang En

AU - Huang, Chan Hui

AU - Chen, Ko Wei

AU - Lee, Chia Jui

AU - Das, Utpal

AU - Jang, Yeong Jiunn

AU - Lin, Wenwei

PY - 2012/8

Y1 - 2012/8

N2 - Organocatalysts bearing sulfide or sulfone functions () were studied for the direct asymmetric Michael addition of ketones and alkylidene malonates. The organocatalyst (S)-2-((naphthalen-2-ylthio)methyl)pyrrolidine, bearing a pyrrolidine and a sulfide moiety, showed a very high catalytic activity in the absence of additives. The reaction condition is mild, and the Michael adducts were obtained in very good enantioselectivities (up to 96%), diastereoselectivities (up to >95:5), and chemical yields (up to 95%). Chirality 24:600-605, 2012. © 2012 Wiley Periodicals, Inc.

AB - Organocatalysts bearing sulfide or sulfone functions () were studied for the direct asymmetric Michael addition of ketones and alkylidene malonates. The organocatalyst (S)-2-((naphthalen-2-ylthio)methyl)pyrrolidine, bearing a pyrrolidine and a sulfide moiety, showed a very high catalytic activity in the absence of additives. The reaction condition is mild, and the Michael adducts were obtained in very good enantioselectivities (up to 96%), diastereoselectivities (up to >95:5), and chemical yields (up to 95%). Chirality 24:600-605, 2012. © 2012 Wiley Periodicals, Inc.

KW - Michael addition

KW - alkylidene malonate

KW - ketones

KW - organocatalysis

KW - stereoselectivity

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DO - 10.1002/chir.22055

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JO - Chirality

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Enantioselective organocatalytic Michael Addition of ketones to alkylidene malonates

Abstract

Keywords

ASJC Scopus subject areas

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