Efficient syntheses of functionalized piperidines through extremely regioselective Rh-catalyzed cyclohydrocarbonylation of amido-ω,ω-dienes

被引：25

作者：

Ojima, I ^{[1
]}

Iula, DM ^{[1
]}

Tzamarioudaki, M ^{[1
]}

机构：

[1] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11794 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 26期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(98)00848-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The highly regioselective cyclohydrocarbonylation of 4-amido-1,6-heptadienes catalyzed by Rh-BIPHEPHOS complex gives functionalized piperidines quantitatively, which serve as versatile intermediates for the syntheses of a variety of piperidine and quinolizidine alkaloids. Reaction of 3-Boc-amino-1,5-hexadiene affords the corresponding dehydropiperidine-aldehyde exclusively via site and regioselective hydroformylation. Possible mechanisms for these reactions are proposed. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4599 / 4602

页数：4

共 15 条

[1]

[Anonymous], 1993, ALKALOIDS CHEM PHARM

[2]

[Anonymous], 1985, ALKALOIDS CHEM BIOL

[3]

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[4] PRACTICAL, HIGH-YIELD, REGIOSELECTIVE, RHODIUM-CATALYZED HYDROFORMYLATION OF FUNCTIONALIZED ALPHA-OLEFINS [J].