Unexpected Electrophilic Rearrangements of Amides: A Stereoselective Entry to Challenging Substituted Lactones | Zendy

Madelaine Claire | Zendy; Valerio Viviana | Zendy; Maulide Nuno | Zendy

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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.

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