Enantioselectively Organocatalytic Michael Addition of Ketones to Alkylidene Malonates

An organocatalytic asymmetric Michael addition of ketones to alkylidene malonates has been developed. In the presence of 20 mol % of urea 1a or N-(pyrrolidin-2-ylmethyl)trifluoromethanesulfonamide 1j, the reactions of ketones with alkylidene malonates afford the desired Michael adducts in moderate t...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 72; no. 11; pp. 4073 - 4076
Main Authors Cao, Chun-Li, Sun, Xiu-Li, Zhou, Jiao-Long, Tang, Yong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.05.2007
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Physical Sciences
Reactivity and mechanisms
Science & Technology
PYRROLIDINE-THIOUREA
ALPHA,BETA-UNSATURATED ALDEHYDES
CONSTRUCTION
NITROOLEFINS
BASE CATALYSTS
FRIEDEL-CRAFTS REACTION
CONJUGATE ADDITIONS
DERIVATIVES
INDOLES
NITROALKENES
Michael addition
Malonic acid derivatives
Sulfonamide
Enantioselectivity
Asymmetric synthesis
Mild operating conditions
Nitrogen heterocycle
Ureas
Ketone
Ethylenic compound
Pyrrolidine derivatives
Online AccessGet full text

Cover

More Information
Summary:An organocatalytic asymmetric Michael addition of ketones to alkylidene malonates has been developed. In the presence of 20 mol % of urea 1a or N-(pyrrolidin-2-ylmethyl)trifluoromethanesulfonamide 1j, the reactions of ketones with alkylidene malonates afford the desired Michael adducts in moderate to good yields with good to high enantioselectivities under mild conditions.
Bibliography:istex:87B91DA036FBD14B02A06F4A762820950262D00E
ark:/67375/TPS-M5GWQHCJ-W
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo070070p