Design and enantioselective synthesis of Cashmeran odorants by using "enol catalysis"
Irene Felker1, Gabriele Pupo, Philip Kraft
1Givaudan Schweiz AG, Fragrance Research, Überlandstrasse 138, 8600 Dübendorf (Switzerland) http://www.givaudan.com.
Abstract:
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.
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