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

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...

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Published in:Nature communications 2020-05, Vol.11 (1), p.2544-2544, Article 2544
Main Authors: Yuan, Zhenbo, Zeng, Yuye, Feng, Ziwen, Guan, Zhe, Lin, Aijun, Yao, Hequan
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Language:English
Subjects:
140/131
140/146
140/58
639/638/403/933
639/638/549/972
639/638/77/883
Alcohols
Alkenes
Amines
Asymmetry
Carbon
Carbonyl compounds
Carbonyls
Cascade chemical reactions
Chemical synthesis
Coupling (molecular)
Cyclopentene
Enantiomers
Humanities and Social Sciences
multidisciplinary
Natural products
Octanes
Palladium
Phenols
Reagents
Science
Science (multidisciplinary)
Transition metals
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description 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. Tandem Heck/carbonylation reaction gives access to ubiquitous carbonyl molecules, however the asymmetric version is rarely studied. Here, the authors synthesize chiral bicyclo[3.2.1]octanes with a palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes with alcohols, phenols and amines.
doi_str_mv 10.1038/s41467-020-16221-9
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subjects 140/131
140/146
140/58
639/638/403/933
639/638/549/972
639/638/77/883
Alcohols
Alkenes
Amines
Asymmetry
Carbon
Carbonyl compounds
Carbonyls
Cascade chemical reactions
Chemical synthesis
Coupling (molecular)
Cyclopentene
Enantiomers
Humanities and Social Sciences
multidisciplinary
Natural products
Octanes
Palladium
Phenols
Reagents
Science
Science (multidisciplinary)
Transition metals
title Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes
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