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Asymmetric Vinylogous Aldol Reaction of α ‐ketoesters with 3‐alkylidene oxindoles
Author(s) -
Kumar Krishna,
Jaiswal Manish K.,
Singh Ravi P.
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700758
Subject(s) - chemistry , cinchona , enantioselective synthesis , aldol reaction , bifunctional , nucleophile , electrophile , yield (engineering) , thiourea , catalysis , organocatalysis , organic chemistry , stereochemistry , medicinal chemistry , materials science , metallurgy
An efficient enantioselective vinylogous aldol reaction of 3‐alkylidene oxindoles with α ‐ketoesters by a bifunctional thiourea catalyst derived from cinchona alkaloid has been disclosed here. The simultaneous H‐bond directing dual activation of vinylogous nucleophile and electrophile afforded high yield (upto 92%) while obtaining excellent stereocontrol (upto 99% ee).