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DOI: 10.1055/s-2004-836022
An Efficient Stereoselective Synthesis of Substituted 1,3-Dienes
Publication History
Publication Date:
12 November 2004 (online)
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Abstract
A stereoselective synthesis of substituted 1,3-dienes has been developed which utilises an Ireland-Claisen rearrangement/silicon-mediated fragmentation sequence. This sequence has been designed to introduce remote centres of asymmetry as well as stereodefined diene systems, and its application to an aziridine system is also described.
Key words
aziridine - Ireland-Claisen rearrangement - Sharpless asymmetric epoxidation - silicon-mediated fragmentation
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References
New address: Kyungsoo Oh, Department of Chemistry, University of Pennsylvania, 231S, 34th Street, Philadelphia, PA 19104, USA.
13A single crystal of 6a of 3,5-dinitrobenzoyl derivative was obtained and the selectivity of 5b and 6b were made from analogy of our Galbonolide study.
16Stereoselective epoxide opening using Ti(i-PrO)4 (Scheme [5] ).
17BF3·OEt2 initiated fragmentation of 9a followed by dehydration of 10a to give 9d (Scheme [6] ).
19Aziridine opening by chloride anion in esterification conditions (Scheme [7] ).
21Conditions using LHMDS and TMSCl-Et3N did not yield any identifiable product.