Selective [3+2] Cycloadditions of β-Amino-α,β-unsaturated Pentacarbonylcarbenechromium Complexes to Alkynes - A New Approach to Functionally Substituted Cyclopentadienes

Bernard L. Flynn; Frank J. Funke; Claudio C. Silveira; Armin de Meijere

doi:10.1055/s-1995-5156

Synlett 1995; 1995(10): 1007-1010
DOI: 10.1055/s-1995-5156

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Selective [3+2] Cycloadditions of β-Amino-α,β-unsaturated Pentacarbonylcarbenechromium Complexes to Alkynes - A New Approach to Functionally Substituted Cyclopentadienes

Bernard L. Flynn, Frank J. Funke, Claudio C. Silveira, Armin de Meijere^*

^*Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, D-37077 Göttingen, Germany

Abstract

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(3-Amino-1-ethoxyalkenylidene)pentacarbonylchromium complexes 2 react with alkynes in pyridine or acetonitrile to give highly substituted 5-amino-3-ethoxycyclopentadienes 3 as formal [3+2]-cycloadducts selectively in high yields rather than the usually favored [2+2+1]-cycloadducts, 5-methylene-2-cyclopenten-1-ones.

Cyclopentadienes, highly substituted - Cyclopentenones, protected - 1-Metalla-1,3,5-hexatrienes - cyclization

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