Conjugate addition of organocopper reagents to gamma-alkoxybutenolides and application to the synthesis of non-racemic alkyl cyclopentenones |
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| Authors: | Robertson Jeremy Menard Morgan Ford Rhonan Bell Stephen |
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| Institution: | Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA. |
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| Abstract: | Simple organocopper reagents are shown to undergo anti-stereoselective 1,4-addition to menthyloxy-substituted lactone 1 in the presence of BF3.OEt2; the Lewis acid causes partial epimerisation of the acetal centre after conjugate addition. Enolate alkylation of the adducts leads to di- and trisubstituted lactones that are converted, in favourable cases, into di- and trisubstituted cyclopentenones. |
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