Diastereoselective synthesis of β-hydroxy-α-phenylcarboxylic esters can be achieved by altering the reaction temperature or solvents during the boron-mediated aldol reaction of methyl phenylacetate. We had reported on the systematic study of enolboration-aldolization of methyl phenylacetate, which revealed that dicyclohexylboron triflate (Chx2BOTf)/Et3N is the most efficient reagent-base combination for the synthesis of anti-aldols. Herein, we report on our study of the effects of the bulk of the enolizing agent on the diastereoselectivity and the development of 9-BBNOTf-mediated, syn-selective aldol reaction of methyl phenylacetate. The details of this study will be discussed.

Reagent-controlled, stereoselective aldol reaction of methyl phenylacetate

2019 Spring National Meeting

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