Stereoselective Lewis Acid Mediated [1,3] Ring Contraction of 2,5‐Dihydrooxepins as a Route to Polysubstituted Cyclopentenes | Zendy

Nasveschuk Christopher G. | Zendy; Rovis Tomislav | Zendy

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Stereoselective Lewis Acid Mediated [1,3] Ring Contraction of 2,5‐Dihydrooxepins as a Route to Polysubstituted Cyclopentenes

Author(s) -

Nasveschuk Christopher G.,

Rovis Tomislav

Publication year - 2005

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.200500088

Subject(s) - lewis acids and bases , contraction (grammar) , modular design , stereoselectivity , chemistry , stereochemistry , ring (chemistry) , computer science , programming language , organic chemistry , philosophy , catalysis , linguistics

A room‐temperature diastereoselective [1,3] rearrangement results from treatment of 2,5‐dihydrooxepins with EtAlCl 2 (see scheme). A modular synthesis of dihydrooxepins allows substituents to be incorporated at any position on the ring, which means that various polysubstituted cyclopentenes can be prepared through this Lewis acid mediated [1,3] ring contraction.

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