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Enantioselective Iridium-Catalyzed Allylic Alkylation Reactions of Masked Acyl Cyanide Equivalents

J. Caleb Hethcox, Samantha E. Shockley and Brian M. Stoltz*

*Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, United States, Email:

J. C. Hethcox, S. E. Shockley, B. M. Stoltz, Org. Lett., 2017, 19, 1527-1529.

DOI: 10.1021/acs.orglett.7b00449


In an enantioselective iridium-catalyzed allylic alkylation reaction of a masked acyl cyanide (MAC) reagent, the umpoled MAC synthon serves as a carbon monoxide equivalent. The reaction proceeds with good yield and excellent selectivity up to gram scale for a wide range of substituted allylic electrophiles to provide enantioenriched vinylated α-aryl carbonyl derivatives.

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Key Words

carboxylic acid derivatives

ID: J54-Y2017