用Sharpless不对称双羟化反应合成手性β-氨基醇  

Application of Sharpless Asymmetric Dihydroxylation to Synthesis of Chiral β-Amino Alcohols

作　　者：柳文敏[1] 刘雪英[1] 宋瑞娟[1] 张生勇[1] 

机构地区：[1]第四军医大学药学系化学教研室,西安710032

出　　处：《有机化学》2006年第3期341-345,共5页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.20372083)资助项目.

摘　　要：以烯烃为原料合成了一组对映体纯的β-氨基醇.在手性配体1,4-双(9-O-奎宁)-2,3-二氮杂萘[(QN)2PHAL]存在下,通过烯烃的Sharpless不对称双羟化、环化、亲核开环和催化氢化等步骤方便地合成了手性β-氨基醇.从环氧化物到氨基醇的总产率为89%～94%,β-叠氮醇和β-氨基醇的光学纯度高达90%～99%ee.同时考察了影响环氧化物开环的各种因素.A series of enantiopure β-amino alcohols were synthesized from the corresponding diols produced by Sharpless asymmetric dihydroxylafion, cyclization of diols, azide opening of epoxides, and catalytic hydrogenation of the resulting azido alcohols. Factors to affect the azide opening of the epoxides were examined. Overall yields from epoxides to amino alcohols were 89%-94%, while enantiomeric excess values of β-azido alcohols and β-amino alcohols were up to 90%-99%.

关 键 词：不对称双羟化 不对称合成 手性邻二醇 手性β-叠氮醇 手性Β-氨基醇 

分 类 号：O621.25[理学—有机化学]