The first catalytic enantioselective Diels-Alder reactions of 1,2-dihydropyridine: efficient syntheses of optically active 2-azabicyclo[2.2.2]octanes with chiral BINAM derived Cr(III) salen complexes

被引：84

作者：

Takenaka, N ^{[1
]}

Huang, Y ^{[1
]}

Rawal, VH ^{[1
]}

机构：

[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA

来源：

TETRAHEDRON | 2002年 / 58卷 / 41期

关键词：

Diels-Alder reaction; enantioselective; alkaloids; asymmetric catalysis; 2-azabicyclo[2.2.2]octane;

D O I：

10.1016/S0040-4020(02)00980-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have synthesized a new family of enantiomerically enriched BINAM-derived Schiff base Cr(III) complexes and evaluated them as catalysts for Diels-Alder reactions. These complexes effectively catalyze, for the first time, the enantioselective Diels-Alder reactions between 1,2-dihydropyridine and N-acryloyloxazolidinone to afford 2-azabicyclo[2.2.2]octanes in high yields (89-99%) and with moderate to good enantioselectivities (79-85%). (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：8299 / 8305

页数：7

共 63 条

[21] Broadly effective enantioselective Diels-Alder reactions of 1-amino-substituted-1,3-butadienes [J].