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Unexpected Electrophilic Rearrangements of Amides: A Stereoselective Entry to Challenging Substituted Lactones
Author(s) -
Madelaine Claire,
Valerio Viviana,
Maulide Nuno
Publication year - 2010
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.200906416
Subject(s) - surprise , stereoselectivity , generality , electrophile , computer science , set (abstract data type) , chemistry , stereochemistry , combinatorial chemistry , information retrieval , psychology , programming language , organic chemistry , communication , psychotherapist , catalysis
Surprise, surprise! An unexpected skeletal rearrangement was developed into a chemo‐ and stereoselective synthesis of α‐allyl and allenyl lactones with challenging substitution patterns (see scheme; EWG=electron‐withdrawing group). The generality, unique features, and synthetic potential of this reaction were probed and a mechanism was proposed.