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Stereoselective Synthesis of Benzoxepines through Tandem Alkylation/Michael Addition to Vinylogous Carbonates
Author(s) -
Gharpure Santosh J.,
Reddy S. Raja Bhushan
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300267
Subject(s) - stereoselectivity , chemistry , alkylation , tandem , steric effects , michael reaction , stereochemistry , organic chemistry , catalysis , materials science , composite material
A tandem S N 2 alkylation/Michael addition to vinylogous carbonates based approach for the stereoselective synthesis of benzoxepines is developed. The stereoselectivity improves with an increase in the steric bulk of the substituents. The method is extended to the synthesis of benzopyranoxepines and benzoxepinopyridines with angular substituents.