ASYMMETRIC DIELS-ALDER REACTIONS CATALYZED BY CHIRAL OXAZABOROLIDINES - EFFECT OF THE POSITION OF AN ELECTRON-DONOR FUNCTIONALITY IN THE ALPHA-SIDE CHAIN SUBSTITUENT ON THE ENANTIOSELECTIVITY

被引：34

作者：

SEERDEN, JPG ^{[1
]}

SCHEEREN, HW ^{[1
]}

机构：

[1] CATHOLIC UNIV NIJMEGEN,NSR,CTR MOLEC STRUCT DESIGN & SYNTH,DEPT ORGAN CHEM,6525 ED NIJMEGEN,NETHERLANDS

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 16期

关键词：

D O I：

10.1016/S0040-4039(00)77652-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric Diels-Alder reactions of cyclopentadiene with methacrolein and 2-bromoacrolein catalyzed by chiral oxazaborolidines 1 derived from N-tosyl-L-alpha-amino acids afforded cycloadducts in quantitative yield. Variation in the position of an electron donor atom in the alpha-side chain substituent shows that enantioselectivity is controlled by the presence of electron donor atoms in position 2 and 4.

引用

页码：2669 / 2672

页数：4