Chiral Primary Amine Catalyzed Asymmetric Tandem Reduction-Michael Addition-Protonation Reaction between Alkylidene Meldrum's Acid and -Substituted Vinyl Ketones

One-pot three-component tandem reduction-Michael addition-protonation reactions of alkylidene Meldrum's acids to -substituted vinyl ketones have been developed by using a chiral primary amine as the organocatalyst, affording the products in excellent yields and with good enantioselectivity.

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 47; no. 15; pp. 2207 - 2216
Main Authors Fu, Niankai, Guo, Yinliang, Zhang, Long, Luo, Sanzhong
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.08.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Michael addition
ELECTROPHILICITY PARAMETERS
ORGANIC-SYNTHESIS
ENANTIOSELECTIVE PROTONATION
enamine protonation
TRANSFER HYDROGENATION
HANTZSCH ESTERS
primary amine catalysis
substituted vinyl ketone
CONSTRUCTION
DIALKYLZINC REAGENTS
Meldrum's acid
DERIVATIVES
CONJUGATE ADDITION
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Summary:One-pot three-component tandem reduction-Michael addition-protonation reactions of alkylidene Meldrum's acids to -substituted vinyl ketones have been developed by using a chiral primary amine as the organocatalyst, affording the products in excellent yields and with good enantioselectivity.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1380717