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Synlett 1995; 1995(12): 1235-1236
DOI: 10.1055/s-1995-5241
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Enantiocomplementary Routes to 6-Oxygenated (2Z,4E)-Alkadiene Precursors via Diastereoselective Reduction of 2-Cyclobuten-1-yl ketones

Kevin J. Hodgetts, Christopher J. Wallis, Timothy W. Wallace*
  • *Department of Chemistry and Applied Chemistry, University of Salford, Salford M5 4WT, U.K.
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Publication Date:
31 December 2000 (online)

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2-Cyclobuten-1-yl methyl ketones are reduced diastereoselectively by hydride reagents to give potential precursors of 6-oxygenated 2,4-alkadienals. Enzymic desymmetrisation of meso-3-cyclobutene-1,2-dimethanol 4 using Pseudomonas fluorescens lipase provides access to the key intermediate, 3-oxabicyclo[3.2.0]hept-6-en-2-one 3, in either enantiomeric form.

Cyclobutenyl ketone - hydride reduction - diastereoselection - Pseudomonas fluorescens lipase - diene synthesis