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Metalated Nitriles: Internal 1,2‐Asymmetric Induction
Author(s) -
Fleming Fraser F.,
Liu Wang,
Ghosh Somraj,
Steward Omar W.
Publication year - 2007
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.200701550
Subject(s) - stereocenter , electrophile , steric effects , moiety , stereoselectivity , chemistry , stereochemistry , vicinal , organic chemistry , enantioselective synthesis , catalysis
Steric screening : In alkylations of metalated nitriles containing vicinal methyl groups and a trisubstituted CC bond, the butene moiety screens electrophilic attack from one diastereotopic face as the quaternary stereocenter is installed (see scheme; LDA=LiN i Pr 2 ). Excellent stereoselectivity is maintained with a wide range of electrophiles to yield acyclic nitriles with contiguous tertiary and quaternary stereocenters.