Diastereoselective Cyclopropanation
of Electron-Deficient Alkenes via Metal Glycal Carbenes

Frank Otto; Karl Heinz Dötz

doi:10.1055/s-2008-1067151

PAPER

Diastereoselective Cyclopropanation of Electron-Deficient Alkenes via Metal Glycal Carbenes

Frank Otto, Karl Heinz Dötz*
Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
Fax: +49(228)735813; e-Mail: doetz@uni-bonn.de;

Abstract

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Abstract

Silyl- and isopropylidene-O-protected chromium glucal and galactal carbenes have been synthesized from their glycal precursors according to the Fischer route. NMR studies indicate a preferred ⁵ H ₄ or ⁴ H ₅ conformation, depending on the nature of the protective group and the configuration at C-4. The complexes with glycal carbenes have been applied to the diastereoselective cyclopropanation of methyl crotonate and γ-crotonolactone.

Key words

carbene complexes - carbohydrates - cycloadditions - diastereoselective synthesis - organometallic reagents

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References

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