TRANS-3,5-DISUBSTITUTEDPYRROLIDINE: ORGANOCATALYST FOR ANTI-MANNICH REACTIONS

摘要

A compound of Formula I is disclosed, in which R is a substituent containing a hydrogen bond-forming atom within three atoms from the ring carbon to which the substituent is bonded; X is CH2, 0, S or NR1, wherein Rl is a hydrocarbyl group or an amino-protecting group having one to about 18 carbon atoms; R2 is hydrido or a hydrocarbyl group containing one to about twelve carbon atoms,- and R3 is hydrido or methyl, but both R2 and R3 are not hydrido when X is CH2 (I) A molecule of Formula I and those in which R2 and R3 can both be hydrido (Formula X) functions as a catalyst in a Mannich reaction to asymmetrically form β- aminoaldehyde or β- aminoketone diastereomeric products having two chiral centers on adjacent carbon atoms and in which the anti- diastereomers are in excess over the syn- diastereomers. Methods for carrying out those syntheses are also disclosed.