发明名称 |
Process for intermediates to 1-carbapenems and 1-carbacephems |
摘要 |
A stereoselective process for chiral intermediates to 1-carbapenum and 1-carbacephalosporins is provided comprising the use of an N-acyl-(4R)-substituted-1,3-thiazolidine-2-thione as a chiral auxiliary in boron enolate mediated aldol condensation with a protected- beta -keto ester aldehyde. E.g., benzyl 3,3-(ethylenedioxy)-4-formylbutyrate is condensed with the boron enolate formed with n-butyryl (4R)-methoxycarbonyl-1,3-thiazolidine-2-thione to provide benzyl 3,3-ethylenedioxy-(5R)-hydroxy-6-[(4R)-methoxycarbonyl-1,3-thiazolidin e-2-thione-3-ylcarbonyl]octanoate. Displacement of the thiazolidine-2-thione chiral auxiliary moiety with an O-alkyl, O-acyl or O-aralkyl hydroxyamine provides the corresponding chiral intermediate as the hydroxamate.
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申请公布号 |
US4745201(A) |
申请公布日期 |
1988.05.17 |
申请号 |
US19850780101 |
申请日期 |
1985.09.25 |
申请人 |
UNIVERSITY OF NOTRE DAME DU LAC |
发明人 |
HSIAO, CHI-NUNG W.;MILLER, MARVIN J. |
分类号 |
C07D317/14;C07D317/00;C07D317/30;C07D405/06;C07D417/06;C07D463/00;C07D477/00;C07F5/02;(IPC1-7):C07D317/26 |
主分类号 |
C07D317/14 |
代理机构 |
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代理人 |
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主权项 |
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地址 |
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