A Novel, Highly Enantioselective Ketone Alkynylation Reaction Mediated by Chiral Zinc Aminoalkoxides
- 1 March 1999
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 38 (5) , 711-713
- https://doi.org/10.1002/(sici)1521-3773(19990301)38:5<711::aid-anie711>3.0.co;2-w
Abstract
Kilogram-scale synthesis of the HIV reverse transcriptase inhibitor efavirenz was achieved by means of a highly enantioselective alkynylation of prochiral ketones 1 with alkynyllithium or alkynylmagnesium reagents in the presence of chiral zinc aminoalkoxides as mediators. With the achiral auxiliary 2,2,2-trifluoroethanol (R3=CF3CH2), the efavirenz precursor 2 (R1=H, R2=cyclopropyl) was obtained with an ee of 99.2%.This publication has 0 references indexed in Scilit: