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Asymmetric Synthesis of Protected Unnatural α-Amino Acids via Enantioconvergent Nickel-Catalyzed Cross-Coupling

Ze-Peng Yang, Dylan J. Freas and Gregory C. Fu*

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

Z.-P. Yang, D. J. Freas, G. C. Fu, J. Am. Chem. Soc., 2021, 143, 8614-8618.

DOI: 10.1021/jacs.1c03903


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Abstract

A chiral catalyst based on nickel, an earth-abundant metal, can achieve the enantioconvergent coupling of readily available racemic alkyl electrophiles with a wide variety of alkylzinc reagents to afford protected unnatural α-amino acids in good yield and ee. This cross-coupling proceeds under mild conditions and is tolerant of air, moisture, and a broad array of functional groups.

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Key Words

α-amino acids


ID: J48-Y2021