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One‐Step Formation both of C–N and of C–O Bonds of N ‐Alkoxyamides through NHC‐Catalyzed Three‐Component Reactions of Enals, Nitrosoarenes, and Enones
Author(s) -
Sun ZhongXin,
Cheng Ying
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200525
Subject(s) - chemistry , organocatalysis , component (thermodynamics) , catalysis , michael reaction , benzoin , condensation , medicinal chemistry , organic chemistry , enantioselective synthesis , physics , thermodynamics
NHC‐catalyzed three‐component reactions of α,β‐unsaturated aldehydes (enals), nitrosoarenes, and α,β‐unsaturated ketones (enones) were studied. The reactions proceeded through a cascade aza‐benzoin condensation/oxo‐Michael addition sequence to produce N , O ‐bisfunctionalized N ‐hydroxylacrylamides in moderate to good yields. This work not only provides an efficient method for the one‐step formation both of the C–N and of the C–O bonds in N ‐alkoxyamides, but also advances the application of NHC organocatalysis in the field of multicomponent reactions.