Stereoselective synthesis of 2-methylenepyrrolizidines by tandem cyclization of N-propargylaminyl radicals

被引：17

作者：

Hasegawa, H ^{[1
]}

Senboku, H ^{[1
]}

Kajizuka, Y ^{[1
]}

Orito, K ^{[1
]}

Tokuda, M ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Engn, Div Mol Chem, Organ Synth Lab, Sapporo, Hokkaido 0608628, Japan

来源：

TETRAHEDRON | 2003年 / 59卷 / 06期

关键词：

tandem radical cyclization; aminyl radical; pyrrolizidine; N-chloroamine;

D O I：

10.1016/S0040-4020(02)01613-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tandem cyclization of N-propargylaminyl radicals, generated by N-chlorination of (E)-alk-4-enylamines 2a-d and 2f followed by treatment with tributyltin radical, afforded 2-methylenepyrrolizidines 3a-d and 3f in a highly stereoselective manner. A similar radical cyclization of (Z)-N-propargyl-1-methyl-5-phenylpent-4-enylamine (2e) gave pyrrolizidine 3b having the same stereochemistry as that obtained from the E isomer 2b. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：827 / 832

页数：6

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