Stereoselective synthesis of anti-beta-amino-alpha-hydroxy acid derivatives using nucleophilic epoxidation of 1-arylthio-1-nitroalkenes

被引:25
作者
Ambroise, L [1 ]
Jackson, RFW [1 ]
机构
[1] UNIV NEWCASTLE UPON TYNE, DEPT CHEM, NEWCASTLE UPON TYNE NE1 7RU, TYNE & WEAR, ENGLAND
关键词
D O I
10.1016/0040-4039(96)00252-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of lithium t-butylperoxide with 1-arylthio-1-nitroalkenes 5, prepared by condensation of (4-tolylthio)nitromethane with N-(Boc)-protected alpha-amino aldehydes, leads to the formation of oxazolidinones rather than the expected oxiranes. Initially. a mixture of c's 8 and trans 9 diastereoisomers is formed, but upon exposure to silica gel complete conversion to the cis-diastereoisomers 8 takes place.
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页码:2311 / 2314
页数:4
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