Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes

Zhenbo Yuan, Yuye Zeng, Ziwen Feng, Zhe Guan, Aijun Lin () and Hequan Yao ()
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Zhenbo Yuan: China Pharmaceutical University
Yuye Zeng: China Pharmaceutical University
Ziwen Feng: China Pharmaceutical University
Zhe Guan: China Pharmaceutical University
Aijun Lin: China Pharmaceutical University
Hequan Yao: China Pharmaceutical University

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract Transition-metal-catalyzed tandem Heck/carbonylation reaction has emerged as a powerful tool for the synthesis of structurally diverse carbonyl molecules, as well as natural products and pharmaceuticals. However, the asymmetric version was rarely reported, and remains a challenging topic. Herein, we describe a palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes. Alcohols, phenols and amines are employed as versatile coupling reagents for the construction of multifunctional chiral bicyclo[3.2.1]octanes with one all-carbon quaternary and two tertiary carbon stereogenic centers in high diastereo- and enantioselectivities. This study represents an important progress in both the asymmetric tandem Heck/carbonylation reactions and enantioselective difunctionalization of internal alkenes.

Date: 2020
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DOI: 10.1038/s41467-020-16221-9

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