Stereocontrolled preparation of chiral secondary α-methylene γ-lactams by addition of organozinc reagents derived from 2-(bromomethy])acrylates to imines using β-aminoalcohols as chiral auxiliaries.
摘要:
Stereocontrolled addition of isolated organozinc reagents 1, prepared from 2-(bromomethyl)acrylates to imines, can be achieved with d.e. approximately 100% using beta-amino alcohols as chiral auxiliaries. High yields of pure R or S secondary alpha-methylene gamma-lactams can be prepared after a three step elimination of the chiral auxiliary (chloration, dehydrochloration of the resulting beta-chloroamine, acid hydrolysis of enamide).
Stereocontrolled preparation of chiral secondary α-methylene γ-lactams by addition of organozinc reagents derived from 2-(bromomethy])acrylates to imines using β-aminoalcohols as chiral auxiliaries.
摘要:
Stereocontrolled addition of isolated organozinc reagents 1, prepared from 2-(bromomethyl)acrylates to imines, can be achieved with d.e. approximately 100% using beta-amino alcohols as chiral auxiliaries. High yields of pure R or S secondary alpha-methylene gamma-lactams can be prepared after a three step elimination of the chiral auxiliary (chloration, dehydrochloration of the resulting beta-chloroamine, acid hydrolysis of enamide).