CONJUGATE ADDITION OF AMINES AND THIOLS TO (R)-1-ACETYL-5-ISOPROPOXY-3-PYRROLIN-2-ONE - PREPARATION OF ENANTIOPURE N-ACYLIMINIUM ION PRECURSORS

被引：32

作者：

KOOT, WJ ^{[1
]}

HIEMSTRA, H ^{[1
]}

SPECKAMP, WN ^{[1
]}

机构：

[1] UNIV AMSTERDAM,ORGAN CHEM LAB,NIEUWE ACHTERGRACHT 129,1018 WS AMSTERDAM,NETHERLANDS

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(00)80435-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Conjugate addition reactions of amines and thiols to enantiopure (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one are shown to proceed with high stereoselectivity. The benzylamine and the benzyl mercaptan adducts were N-deacylated and then treated with Lewis acid to effect N-acyliminium cyclization. This cyclization proceeded smoothly with the benzyl mercaptan adduct. The benzylamine adduct only cyclized after amine protection with the Boc group, but then led to an enantiopure oxazolidinone.

引用

页码：1941 / 1948

页数：8

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