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Oxonitriles: Multicomponent Grignard Addition–Alkylations
Author(s) -
Fleming Fraser F.,
Zhang Zhiyu,
Wang Qunzhao,
Steward Omar W.
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200352920
Subject(s) - conjugate , alkylation , stereocenter , chelation , chemistry , combinatorial chemistry , computer science , organic chemistry , enantioselective synthesis , catalysis , mathematics , mathematical analysis
Three at a time : Sequential carbonyl addition, chelation‐controlled conjugate addition, and alkylation triggers the multicomponent assembly of diverse nitriles. The chelation‐controlled conjugate addition–alkylation installs three new stereocenters (see scheme), thereby generating substituted nitriles that are ideal terpenoid precursors as illustrated in the synthesis of epi ‐dehydroabietic acid.