Systematic Study and Selected Applications of the Enolboration-Aldolization of Substituted Acetic Acids
Reported herein is the systematic study of the enolboration-aldolization of selected substituted acetic acids. The study has revealed protocols for the synthesis of highly anti-selective β-hydroxy acids. While most reported boron mediated aldols are limited to aldehydes, these protocols provided good yields and excellent diastereoselectivities of the ketone aldols as well. The study included 3,3,3-trifluoropropanoic acid wherein the α-trifluoromethyl-β-hydroxy acids obtained were used to achieve the successful synthesis of the novel α-trifluoromethyl-β-lactones as well as (E)-1-trifluoromethyl alkenes. The formal synthesis of tetrahydrolipstation and venlafaxine were also achieved in good yields via variations of the protocol.
Ramachandran, Purdue University.
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