Patent ID: 6448409
Filing Date: 2002-09-10
Classification: C07B,C07D

Abstract:
An aldol condensation synthesis method for generating a two chiral center compound that is selectively a syn or anti 1,2-diol containing product isomer, comprising the steps:a) obtaining a chiral 2-oxazolidineselone as an aldol acceptor; b) mixing said obtained chiral 2-oxazolidineselone with a first quantity of Lewis acid and reacting for a first reaction period; c) mixing with said first reaction period mixture an amine and reacting for a second reaction period to generate an enolate solution; d) mixing with said enolate solution an aldehyde as an aldol donor and reacting for a third reaction period to favor selectively producing the syn isomer product or producing no diastereoselectivity or mixing with said aldol donor that is precomplexed with a second quantity of said Lewis acid and reacting for said third reaction period to favor selectively producing the anti isomer product, wherein said syn or anti isomer product contains a selone auxiliary; e) quenching with a proton source said third reaction period mixture; f) removing the selone auxiliary to produce the two chiral center compound that is selectively a syn or anti 1,2-diol containing isomer product; and g) isolating the syn or anti 1,2-diol containing isomer product.