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Stereoselective Intramolecular Alkylation of Glycosylimides to Highly Functionalized Bicyclic 2,5‐Azepanediones and Heterotricyclic [5.3.1.0 2, 6 ]undecanamides
Author(s) -
Sowa Carsten Endres,
Thiem Joachim
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199419791
Subject(s) - bicyclic molecule , intramolecular force , regioselectivity , alkylation , stereoselectivity , chemistry , stereochemistry , organic chemistry , catalysis
An intramolecular, stereoselective alkylation for monosaccharides is obtained by irradiation of glycosylimides with UV light. The regiochemistry of the central Norrish type II hydrogen abstraction can be controlled by the choice of saccharides and protecting groups. In this way the bicyclic and tricyclic compounds 1 and 2 , respectively, become accessible. R = t BuMe 2 Si.