Preparation of optically active 2,3-diarylepoxide compounds comprises epoxidizing diaryl compounds and optionally separating the obtained enantiomeric mixture

摘要

Preparation of optically active 2,3-diarylepoxide compounds (Ia)-(Id) comprises epoxidizing diaryl compounds (IIa) or (IIb) and optionally separating the obtained enantiomeric mixture. Preparation of optically active 2,3-diarylepoxide compounds of formula (Ia)-(Id) comprises epoxidizing diaryl compounds of formula (IIa) or (IIb) and optionally separating the obtained enantiomeric mixture. R : CH2X, CHO, CH=NR1, CH=NNR2, COOH, COOR3, CONR4R5 or CN; X : OH, O-SO2R6 or halo; R1H, OH, 1-8C-alkyl or aryl; R2H, 1-8C-alkyl or aryl; R31-8C-alkyl, 2-8C-hydroxyalkyl or arylalkyl; either R4, R5H, 1-8C-alkyl, 2-8C-hydroxyalkyl, aryl or arylalkyl; or R4R5N : 5-6 membered (un)saturated ring with 1-3 heteroatoms; and R61-8C (halo)alkyl or aryl. Independent claims are included for: (1) new 2,3-diarylepoxide compounds (Ia)-(Id); and (2) preparation of (1,2,4)triazol-1-ylmethyloxirane compounds of formula (IIIa) or (IIIb) comprising either reductive amination of (Ia) or (Ib) (when R is CHO) in the presence of 1H-(1,2,4)triazole or reduction of (Ia) or (Ib) (when R is CONR4R5 and NR4R5 form a 1H-(1,2,4)triazole-1-yl ring). Provided that: (a) in (Ia) and (Ib) R is not CH2X or COOH; and (b) R4 and R5 may also be 1-8C hydroxyalkyl. [Image] [Image] [Image].