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.
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页码：1745 / 1756
页数：12
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