Preparation and application of 2-(arylmethoxy)isopinocampheols for the asymmetric aldol reaction of 3,3,3-trifluoropropionates |
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| Authors: | P Veeraraghavan Ramachandran Gowrisankar ParthasarathyPravin D Gagare |
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| Institution: | Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084, USA |
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| Abstract: | The preparation of 2-(arylmethoxy)isopinocampheols from pinanediol via the DIABL-H reduction of the corresponding aryl aldehyde acetals has been described. A systematic examination of the asymmetric aldol reaction of 3,3,3-trifluoropropionates led to the double diastereoselective aldol reaction of 2-(arylmethoxy)isopinocampheyl 3,3,3-trifluoropropionates providing anti-α-trifluoromethyl-β-hydroxy esters in 63-85% yields, ?99% anti-selectivity and 80-96% de for the anti-isomer. |
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| Keywords: | Aldol Trifluoropropionates Boron enolates Isopinocampheols Diisopinocampheylboron triflate |
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