发明名称 |
Aziridine compounds, methods of preparation and reactions thereof |
摘要 |
Novel N-sulfinyl-2-carboxyaziridine compounds and novel N-hydrogen-2-hydroxymethylaziridine compounds are provided. The asymmetric synthesis of N-sulfinylaziridines is readily accomplished in high diastereomeric purity and good yield by the Darzens-type reaction of the metal enolate of an alpha -haloester and an enantiopure sulfinimine. Ring-opening of these aziridines affords alpha -amino acids and the otherwise difficult to prepare syn- beta -hydroxy- alpha -amino acids, both key structural units found in many bioactive materials. The N-sulfinyl radical may be selectively removed from the novel aziridine compounds by treatment with acid or base. Alternatively, the N-sulfinyl radical may be oxidized to provide the corresponding N-sulfonyl-aziridine, or reduced to form the corresponding 1H-2-hydroxymethylaziridine, either of which may subsequently be ring-opened to provide precursors to bioactive compounds.
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申请公布号 |
US5789599(A) |
申请公布日期 |
1998.08.04 |
申请号 |
US19940239097 |
申请日期 |
1994.05.06 |
申请人 |
DREXEL UNIVERSITY |
发明人 |
DAVIS, FRANKLIN A.;ZHOU, PING;REDDY, GADDAMPALLY VENKAT |
分类号 |
C07C315/02;C07C317/46;C07C319/20;C07C323/41;C07D203/08;C07D203/24;(IPC1-7):C07D203/24 |
主分类号 |
C07C315/02 |
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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