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%.
|Original language||English (US)|
|Number of pages||3|
|Journal||Angewandte Chemie - International Edition|
|State||Published - Mar 1 1999|
All Science Journal Classification (ASJC) codes
- Amino alcohols
- Nucleophilic additions