New enantiomerically pure 1,2-dihydropyridine and its use for construction of optically active 2-azabicycio[2.2.2] octane

被引：43

作者：

Matsumura, Y ^{[1
]}

Nakamura, Y ^{[1
]}

Maki, T ^{[1
]}

Onomura, O ^{[1
]}

机构：

[1] Nagasaki Univ, Fac Pharmaceut Sci, Nagasaki 8528521, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 40期

关键词：

Diels-Alder reactions; nitrogen heterocycles; amino acids and derivatives; asymmetric synthesis;

D O I：

10.1016/S0040-4039(00)01342-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantiomerically pure 1,2-dihydropyridine 1 was prepared from L-lysine utilizing anodic oxidation as a key step, and was utilized as a chiral diene synthon of the Diels-Alder reaction. Furthermore, a suitable condition for the Diels-Alder reaction between 1 and N-acryloyloxazolidinone (8) was exploited. That is, the presence of AlCl3 efficiently promoted the Diels-Alder reaction to give a cycloadduct with high stereoselectivity, which was converted to an optically active 2-azabicyclo[2.2.2]octane derivative 2 (96.8% ee). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7685 / 7689

页数：5

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