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

页码：107 / 111

页数：5

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