1187159-14-3Relevant academic research and scientific papers
Asymmetric tandem Wittig rearrangement/aldol reactions
Giampietro, Natalie C.,Kampf, Jeff W.,Wolfe, John P.
supporting information; experimental part, p. 12556 - 12557 (2010/01/29)
(Chemical Equation Presented) A new method for the asymmetric synthesis of α-alkyl-α,β-dihydroxy esters that involves tandem Wittig rearrangement/aldol reactions of O-benzyl- or O-allylglycolate esters derived from 2-phenylcyclohexanol is described. This sequence constructs two C-C bonds and two stereocenters, one of which is quaternary, to afford syn diol products with excellent stereocontrol. Cleavage of the chiral auxiliary affords enantiomerically enriched products with up to 95% ee. The application of this method to the preparation of a key intermediate in the synthesis of the antifungal agent alternaric acid is also described.
