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Design and Enantioselective Synthesis of Cashmeran Odorants by Using “Enol Catalysis”
Author(s) -
Felker Irene,
Pupo Gabriele,
Kraft Philip,
List Benjamin
Publication year - 2015
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.201409591
Subject(s) - enantiopure drug , enantioselective synthesis , stereocenter , enol , enantiomer , chemistry , catalysis , stereochemistry , stereoisomerism , combinatorial chemistry , organic chemistry
Novel Cashmeran odorants were designed by molecular modeling. Their short syntheses involve a novel asymmetric Brønsted acid catalyzed Michael addition of unactivated α‐substituted ketones. This key transformation was realized by utilizing a new type of enol activation catalysis and affords different cyclic ketones bearing α‐quaternary stereocenters in good to excellent yields and with high enantioselectivity. Subsequent McMurry coupling and Saegusa–Ito oxidation furnished the enantiopure target odorants, one enantiomer of which indeed possesses the typical olfactory aspects of Cashmeran.