Towards a Catalytic Asymmetric
Version of the [3+2] Cycloaddition between Hydrazones
and Cyclopentadiene

Alexandru Zamfir; Svetlana B. Tsogoeva

doi:10.1055/s-0030-1260467

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Synthesis 2011(12): 1988-1992
DOI: 10.1055/s-0030-1260467

PAPER

Towards a Catalytic Asymmetric Version of the [3+2] Cycloaddition between Hydrazones and Cyclopentadiene

Alexandru Zamfir, Svetlana B. Tsogoeva*
Department of Chemistry and Pharmacy, Institute of Organic Chemistry I, University of Erlangen-Nuremberg, Henkestr. 42, 91054 Erlangen, Germany
Fax: +49(9131)8526865; e-Mail: tsogoeva@chemie.uni-erlangen.de;

Further Information

Publication History

Received 12 April 2011
Publication Date:
17 May 2011 (online)

Abstract
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Abstract

A novel and easily accessible metal-free catalytic system, an in situ generated BINOL-phosphate-derived silicon Lewis acid, has been described for the [3+2] cycloaddition of N-benzoylhydrazone to cyclopentadiene to afford a cycloadduct in high diastereomeric ratio of 95:5 (syn/anti) and enantiomeric excess of 89%. These results provide insights in the future design and development of highly active and enantioselective silicon Lewis acids for this and other cycloaddition types.

Key words

cycloaddition - silicon - hydrazones - Lewis acids - nitrogen heterocycles

References

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11

3-Phenylpropionaldehyde derived hydrazones with other protecting groups like BOC (tert-butyloxycarbonyl) or Ac(acetyl) showed no or little reactivity.