X-ray crystallographic proof of regioselectivity in a nitrosobenzene cycloaddition, and development of a novel in situ heterocycloaddition trap for use during decomplexation of tricarbonyliron diene complexes in hippeastrine synthesis

被引：11

作者：

Anson, CE ^{[1
]}

Hartmann, S ^{[1
]}

Kelsey, RD ^{[1
]}

Stephenson, GR ^{[1
]}

机构：

[1] Univ E Anglia, Sch Chem Sci, Norwich NR4 7TJ, Norfolk, England

来源：

POLYHEDRON | 2000年 / 19卷 / 05期

关键词：

nitrosobenzene cycloaddition; regioselectivity; organoiron compounds; decomplexation; heterocycloaddition trap; alkaloid synthesis;

D O I：

10.1016/S0277-5387(99)00410-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The heterocycloaddition reaction between nitrosobenzene and 2-methylcyclohexa-1,3-diene preferentially affords the regioisomer with the N-Ph group next to the methyl substituent, and this product has been characterised by X-ray crystallography. As a model study for a tricarbonyliron mediated route to the alkaloid hippeastrine, a 2-methyl-6-phenylcyclohexadiene analogue has been prepared from tricarbonyl(eta(5)-3-methylcyclohexadienyl) iron(1+) hexafluorophosphate(1-) and has been examined in the heterocycloaddition reaction. A novel in situ heterocycloaddition trapping procedure has been developed based on this chemistry. Tricarbonyl(eta(4)-2-methyl-6-phenylcyclohexadiene)iron(0) can be converted directly into the cycloadduct in this way by reaction with trimethylamine N-oxide in the presence of nitrosobenzene. (C) 2000 Elsevier Science Ltd All rights reserved.

引用

页码：569 / 571

页数：3

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