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Convergent Catalytic Asymmetric Synthesis of Esters of Chiral Dialkyl Carbinols

Ze-Peng Yang and Gregory C. Fu*

*Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States, Email:

Z.-P. Yang, G. C. Fu, J. Am. Chem. Soc., 2020, 142, 5870-5875.

DOI: 10.1021/jacs.0c01324

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An enantioselective Ni-catalyzed reaction of an alkyl halide (derived from an aldehyde and an acyl bromide), an olefin, and a hydrosilane provides esters of chiral dialkyl carbinols. The method is versatile and tolerates substituents that vary in size and that bear a range of functional groups. A four-component variant of this process, wherein the alkyl halide is generated in situ, is also reported.

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Key Words

alcohols, triethoxysilane, terminal olefins, benzoyl-protected alcohols

ID: J48-Y2020