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A Novel, Highly Enantioselective Ketone Alkynylation Reaction Mediated by Chiral Zinc Aminoalkoxides
Author(s) -
Tan Lushi,
Chen Chengyi,
Tillyer Richard D.,
Grabowski Edward J. J.,
Reider Paul J.
Publication year - 1999
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/(sici)1521-3773(19990301)38:5<711::aid-anie711>3.0.co;2-w
Subject(s) - enantioselective synthesis , alkynylation , ketone , zinc , chemistry , combinatorial chemistry , organic chemistry , catalysis
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 (R 3 =CF 3 CH 2 ), the efavirenz precursor 2 (R 1 =H, R 2 =cyclopropyl) was obtained with an ee of 99.2%.