OXIDATIVE PREPARATION OF OPTICALLY-ACTIVE N-HYDROXY-ALPHA-AMINO ACID-AMIDES

被引：27

作者：

FEENSTRA, RW

STOKKINGREEF, EHM

REICHWEIN, AM

LOUSBERG, WBH

OTTENHEIJM, HCJ

KAMPHUIS, J

BOESTEN, WHJ

SCHOEMAKER, HE

MEIJER, EM

机构：

[1] CATHOLIC UNIV NIJMEGEN,DEPT ORGAN CHEM,6525 ED NIJMEGEN,NETHERLANDS

[2] DSM RES & PATENTS,DEPT BIOORGAN CHEM,6160 MD GELEEN,NETHERLANDS

来源：

TETRAHEDRON | 1990年 / 46卷 / 05期

关键词：

D O I：

10.1016/S0040-4020(01)81979-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two routes are presented for the conversion of optically active α-amino acid amides into the title compounds. One route(route A) features the formation of the Schiff's base 6 which is subsequently oxidized to the corresponding oxaziridines 7. Route B is characterized by the formation of an imidazolin 11 which is hydroxylated to compound 12. Alcoholysis of 7 and 12 in the presence of hydroxylamine hydrochloride yields the title compounds in overall yields ringing from 65 to 85%(route A) and from 14 to 21%(route B). © 1990.

引用

页码：1745 / 1756

页数：12

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