Enzyme and Palladium Catalysis as a Powerful Combination in Asymmetric Transformations ofmeso-2-Alkene-1,4-diol Derivatives. Application to Enantiodivergent Synthesis of (R)- and (S)-(2,4-Cycloalkadienyl)acetic Acids
- 1 January 1993
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1993 (03) , 343-348
- https://doi.org/10.1055/s-1993-25862
Abstract
Enzymatic hydrolysis of meso-diacetates cis-1,4-diacetoxy-2-cyclohexene (4a) and cis-1,4-diacetoxy-2-cycloheptene (4b) was used to prepare enantiomerically pure (> 98 % ee) 4-acetoxy-2-cyclohexenol (5a) and 4-acetoxy-2-cycloheptenol (5b), respectively. The latter compounds 5 are useful synthons for further functionalization via Pd(0)-catalyzed nucleophilic substitution. Using palladium chemistry it was possible to direct the nucleophilic substitution of either of the allylic oxygen groups to selectively obtain both enantiomers of the product. This methodology was applied to the enantiodivergent synthesis of diene acids (S)- 10 and (R)- 10, which were transformed to enantiomeric lactones via a palladium-catalyzed oxidation.Keywords
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