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1. (WO1998051676) EFFICIENT ENANTIOSELECTIVE ADDITION REACTION USING AN ORGANOZINC REAGENT

Pub. No.:    WO/1998/051676    International Application No.:    PCT/US1998/008888
Publication Date: Fri Nov 20 00:59:59 CET 1998 International Filing Date: Wed May 13 01:59:59 CEST 1998
IPC: C07C 215/68
C07D 265/18
Applicants: MERCK & CO., INC.
CHEN, Cheng, Yi
TILLYER, Richard, D.
TAN, Lushi
Inventors: CHEN, Cheng, Yi
TILLYER, Richard, D.
TAN, Lushi
Title: EFFICIENT ENANTIOSELECTIVE ADDITION REACTION USING AN ORGANOZINC REAGENT
Abstract:
An efficient method for the preparation of key intermediate, in the synthesis of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one, a reverse transcriptase inhibitor is achieved using a chiral addition reaction to the 4-chloro-2-trifluoromethylketoaniline with an organozinc complex to give the desired alcohol. This instant method has broad applicability in the chiral addition to any prochiral ketone.