Copper-catalysed asymmetric reductive cross-coupling of prochiral alkenes

Wan Seok Yoon, Won Jun Jang, Woojin Yoon, Hoseop Yun () and Jaesook Yun ()
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Wan Seok Yoon: Sungkyunkwan University
Won Jun Jang: Sungkyunkwan University
Woojin Yoon: Ajou University
Hoseop Yun: Ajou University
Jaesook Yun: Sungkyunkwan University

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract Asymmetric construction of C(sp3)–C(sp3) bond with good stereocontrol of the two connecting carbon centres retaining all carbon or hydrogen substituents is a challenging target in transition metal catalysis. Transition metal-catalysed reductive coupling of unsaturated π-substrates is considered as a potent tool to expediently develop the molecular complexity with high atom efficiency. However, such an asymmetric and intermolecular process has yet to be developed fully. Herein, we report an efficient strategy to reductively couple two prochiral conjugate alkenes using a copper-catalysed tandem protocol in the presence of diboron. Notably, this transformation incorporates a wide range of terminal and internal enynes as coupling partners and facilitates highly diastereo- and enantioselective synthesis of organoboron derivatives with multiple adjacent stereocentres in a single operation.

Date: 2022
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DOI: 10.1038/s41467-022-30286-8

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