Photoinduced, Copper-Catalyzed Enantioconvergent Alkylations of Anilines by Racemic Tertiary Electrophiles: Synthesis and Mechanism
Hyungdo Cho, Hidehiro Suematsu, Paul H. Oyala, Jonas C. Peters* and Gregory C. Fu*
*Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States, Email: jpeterscaltech.edu, gcfucaltech.edu
H. Cho, H. Suematsu, P. H. Oyala, J. C. Peters, G. C. Fu, J. Am. Chem. Soc., 2022, 144, 4550-4558.
DOI: 10.1021/jacs.1c12749
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Abstract
A readily accessible chiral copper catalyst can achieve a photoinduced, enantioconvergent coupling of a variety of racemic tertiary alkyl electrophiles with aniline nucleophiles to generate a new C-N bond with good ee at the fully substituted stereocenter of the product.
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proposed mechanism
(R)-DTBM-SEGPHOS / BTPP
Key Words
α-amino nitriles, photochemistry
ID: J48-Y2022