Highly Enantio- and Diastereoselective Inverse Electron Demand Hetero-Diels-Alder Reaction using 2-Alkenoylpyridine N-Oxides as Oxo-Heterodienes

被引：42
作者：
Barroso, Santiago [1 ]
Blay, Gonzalo [1 ]
Carmen Munoz, M. [2 ]
Pedro, Jose R. [1 ]
机构：
[1] Univ Valencia, Dept Quim Organ, Fac Quim, E-46100 Burjassot, Spain
[2] Univ Politecn Valencia, Dept Fis Aplicada, E-46071 Valencia, Spain
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 1-2期
关键词：
asymmetric catalysis; cycloaddition; hetero-Diels-Alder reaction; oxygen heterocycles; pyridines; WATER-ENHANCED ENANTIOSELECTIVITY; ASYMMETRIC-SYNTHESIS; DANISHEFSKYS DIENE; VINYL ETHERS; ALDEHYDES; DERIVATIVES; KETONES; COMPLEXES; CATALYSIS; BIOSYNTHESIS;
D O I：
10.1002/adsc.200800606
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A general catalytic inverse electron demand hetero-Diels Alder reaction for 2-alkenoylpyridine N-oxides is presented. 2-Alkenoylpyridine N-oxides react very efficiently with alkenes in the presence of bisoxazolidine-copper(II) [BOX-Cu(II)] complexes to give chiral dihydropyrans bearing a pyridine ring at the 6-position with very high yields and excellent diastereo- and enantioselectivity. These heterodienes exhibited higher reactivity and enantioselectivity than the corresponding non-oxidized 2-alkenoylpyridines.
引用
收藏
页码：107 / 111
页数：5
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