AN ACCESS TO ERYTHRO-DIOLS VIA SHARPLESS ASYMMETRIC DIHYDROXYLATION REACTION

被引:25
作者
KO, SY
MALIK, M
DICKINSON, AF
机构
[1] Sandoz Institute for Medical Research, London WC1E 6BN
关键词
D O I
10.1021/jo00088a045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method has been developed to access erythro-2,3-diols via Sharpless's asymmetric dihydroxylation reaction. Thus, a TBDMS-protected (E)-allylic alcohol is dihydroxylated and the resulting threo-2,3-diol is converted to the cyclic sulfate. Upon desilylation, this compound undergoes a Payne-type rearrangement. Nucleophilic epoxide-opening then provides an erythro-2,3-diol. The conversions from the cyclic sulfate to the diol product are performed in a single reaction vessel. Due to the irreversible nature of the Payne-type rearrangement, this process is easy to perform and completely regioselective independent of the substrate structures. Also, being performed in THF, the process is compatible with a variety of nucleophiles, including thiolates, N--(3), (OAc)-O--, (CN)-C--, halides as well as carbon nucleophiles and hydride.
引用
收藏
页码:2570 / 2576
页数:7
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