Premium
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.