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Synthesis 2006(3): 471-479
DOI: 10.1055/s-2006-926276
DOI: 10.1055/s-2006-926276
PAPER
© Georg Thieme Verlag Stuttgart · New YorkHighly Diastereoselective Sequential Michael-Aldol Reactions of Methyl 2-Chloro-2-cyclopropylideneacetate with Grignard Reagents and Aldehydes [1]
Further Information
Received
18 May 2005
Publication Date:
11 January 2006 (online)
Publication History
Publication Date:
11 January 2006 (online)
Abstract
Grignard reagents, especially isopropylmagnesium chloride, smoothly undergo Michael addition onto methyl 2-bromo- and 2-chloro-2-cyclopropylideneacetate (1-Cl), and the thus formed magnesium enolates are particularly efficiently trapped with aromatic aldehydes. This one-pot reaction provides highly substituted chlorohydrines, mostly in high yields (10 out of 18 examples with 72-92%) and as pure (2S*,3R*)-diastereomers (anti-aldols). These chlorohydrines can be transformed to Darzens-type α,β-epoxyesters in good yields, as demonstrated for one example.
Key words
small ring systems - Michael additions - aldol reactions - domino reactions - diastereoselectivity - synthetic methods
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Part 119 in the series ‘Cyclopropyl Building Blocks for Organic Synthesis’.
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Part 117: Bräse, A.; Nüske, H.; Frank, D.; de Meijere, A. Eur. J. Org. Chem. 2005, 4167.
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References
Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited as supplementary publication no. CCDC-268832 with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44 (1223)336033; E-mail: deposit@ccdc.cam.ac.uk].