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%.
CITATION STYLE
Tan, L., Chen, C. Y., Tillyer, R. D., Grabowski, E. J. J., & Reider, P. J. (1999). A novel, highly enantioselective ketone alkynylation reaction mediated by chiral zinc aminoalkoxides. Angewandte Chemie - International Edition, 38(5), 711–713. https://doi.org/10.1002/(SICI)1521-3773(19990301)38:5<711::AID-ANIE711>3.0.CO;2-W
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