Enantioselective synthesis of unsymmetrical benzoins from (S)-mandelic acid enolate and aromatic aldehydes |
| |
Authors: | Gonzalo Blay |
| |
Affiliation: | Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, E-46100 Burjassot (València), Spain |
| |
Abstract: | The reaction of the lithium enolate of the 1,3-dioxolan-4-one derived from optically active (S)-mandelic acid and pivalaldehyde with aromatic aldehydes proceeds readily to give the corresponding aldol products in good yields and diastereoselectivities. Subsequent hydroxyl protection, basic hydrolysis of the dioxolanone, oxidative decarboxylation of the α-hydroxyacid moiety, and hydroxyl deprotection provides chiral unsymmetrical benzoins with high enantiomeric excesses. |
| |
Keywords: | Dioxolanones Self-regeneration of stereocenters Aldol reaction Oxidative decarboxylation |
本文献已被 ScienceDirect 等数据库收录! |
|