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Synthesis 2011(17): 2751-2753  
DOI: 10.1055/s-0030-1260161
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Triple Mukaiyama-Michael Cascade toward a Tricyclic Framework

Dina Shpasser, Moshe Kapon, Mark Botoshansky, Moris S. Eisen*
Schulich Faculty of Chemistry and Institute of Catalysis Science and Technology, Technion-Israel Institute of Technology, Haifa 32000, Israel
Fax: +972(4)8295705; e-Mail: chmoris@tx.technion.ac.il;
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Publication History

Received 28 April 2011
Publication Date:
05 August 2011 (online)

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Abstract

The intermolecular Mukaiyama-Michael addition between stoichiometric amounts of a bisketene acetal and methyl vinyl ketone is rapidly followed by a double cascade intramolecular Mukaiyama-Michael addition to form a fused tricyclic compound containing four-, five- and six-membered rings embellished with several functionalities.

Key words

Mukaiyama-Michael addition - cascade reaction - fused tricyclic framework - silyl enol ethers - bisketene acetals

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Crystallographic data for the structure 6 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 821687. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.