Elsevier

Tetrahedron Letters

Volume 52, Issue 41, 12 October 2011, Pages 5359-5362
Tetrahedron Letters

Preparation and application of 2-(arylmethoxy)isopinocampheols for the asymmetric aldol reaction of 3,3,3-trifluoropropionates

https://doi.org/10.1016/j.tetlet.2011.08.034Get rights and content

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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Acknowledgment

Financial support from the Herbert C. Brown Center for Borane Research is gratefully acknowledged.

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