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Stereoselective Synthesis of Benzomorphan Derivatives with Perpivaloylated Galactose as the Chiral Auxiliary
Author(s) -
Klegraf Ellen,
Knauer Stephan,
Kunz Horst
Publication year - 2006
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.200504090
Subject(s) - stereoselectivity , regioselectivity , chemistry , galactose , sugar , stereochemistry , organic chemistry , catalysis
“Which way, sugar?” The cyclization of benzyl‐substituted N ‐galactosyl didehydropiperidinones leads stereoselectively to regioisomerically annelated and highly substituted benzomorphan derivatives, which are pharmacophorically relevant structural elements (see scheme). The perpivaloylated N ‐galactosyl auxiliary controls the stereo‐ as well as the regioselectivity of the reaction.