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

Access to Document

10.1002/chir.22055

Cite this

@article{fdf5cdda81994d14b86bc4c842ddb594,

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",

year = "2012",

month = aug,

doi = "10.1002/chir.22055",

language = "English",

volume = "24",

pages = "600--605",

journal = "Chirality",

issn = "0899-0042",

publisher = "Wiley-Liss Inc.",

number = "8",

}

TY - JOUR

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

UR - https://www.scopus.com/pages/publications/84864416373

UR - https://www.scopus.com/pages/publications/84864416373#tab=citedBy

U2 - 10.1002/chir.22055

DO - 10.1002/chir.22055

M3 - Article

C2 - 22589149

AN - SCOPUS:84864416373

SN - 0899-0042

VL - 24

SP - 600

EP - 605

JO - Chirality

JF - Chirality

IS - 8

ER -

Enantioselective organocatalytic Michael Addition of ketones to alkylidene malonates

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this