Synfacts 2020; 16(07): 0797
DOI: 10.1055/s-0040-1707028
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Enantioconvergent Coupling of Racemic Partners

Mark Lautens
Randy Sanichar
Huo N, Gorsline BJ, Fu GC. * California Institute of Technology, Pasadena, USA
Catalyst-Controlled Doubly Enantioconvergent Coupling of Racemic Alkyl Nucleophiles and Electrophiles.

Science 2020;
367: 559-564
Further Information

Publication History

Publication Date:
17 June 2020 (online)



Fu and co-workers report a nickel-catalyzed doubly enantioconvergent alkyl–alkyl coupling of racemic partners that proceeds with unprecedented selectivity. The authors employed a chiral nickel catalytic system that generates the product as a single stereoisomer from racemic propargylic halides and racemic β-zincated amides.



The authors propose that the enantioconvergence of the starting materials is facilitated by a radical intermediate arising from both starting materials. The presence of radical intermediates was inferred by the TEMPO adducts formed from both the electrophile and nucleophile partners in the mechanistic study.