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A novel stereocontrolled synthesis of cis-fused bicyclic lactams via [3 + 2]-cycloaddition of alkynyltungsten complexes with tethered aziridines
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A novel stereocontrolled synthesis of cis-fused bicyclic lactams via [3 + 2]-cycloaddition of alkynyltungsten complexes with tethered aziridines

Reniguntala J. Madhushaw, Chu-Chen Hu and Rai-Shung Liu
Organic Letters, Vol.4(23), pp.4151-4153
14/11/2002

Abstract

(matrix presented) Treatment of alkynyltungsten complexes with tethered aziridines in the presence of BF 3 ·Et 2 O led to [3 + 2]-cycloaddition reactions, affording bicyclic tungsten-enamine species stereoselectively. The stereochemistry of the resulting product reveals that ring opening of aziridine is initiated by S N 2 attack of the tungsten fragment. Decomplexation of these organometallics with I 2 in CH 2 C 2 , followed by hydrolysis, afforded only cis-fused bicyclic lactams efficiently.

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