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

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

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 alcohol...

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Main Authors: Zhenbo Yuan, Yuye Zeng, Ziwen Feng, Zhe Guan, Aijun Lin, Hequan Yao
Format: Article
Language:English
Published: Nature Publishing Group 2020-05-01
Series:Nature Communications
Online Access:https://doi.org/10.1038/s41467-020-16221-9
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spelling doaj-8db740ae56e844d88c1f4318a0aea4032021-05-23T11:15:30ZengNature Publishing GroupNature Communications2041-17232020-05-011111810.1038/s41467-020-16221-9Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenesZhenbo Yuan0Yuye Zeng1Ziwen Feng2Zhe Guan3Aijun Lin4Hequan Yao5State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical UniversityState Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical UniversityState Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical UniversityState Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical UniversityState Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical UniversityState Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical UniversityTandem 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.https://doi.org/10.1038/s41467-020-16221-9
collection DOAJ
language English
format Article
sources DOAJ
author Zhenbo Yuan
Yuye Zeng
Ziwen Feng
Zhe Guan
Aijun Lin
Hequan Yao
spellingShingle Zhenbo Yuan
Yuye Zeng
Ziwen Feng
Zhe Guan
Aijun Lin
Hequan Yao
Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes
Nature Communications
author_facet Zhenbo Yuan
Yuye Zeng
Ziwen Feng
Zhe Guan
Aijun Lin
Hequan Yao
author_sort Zhenbo Yuan
title Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes
title_short Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes
title_full Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes
title_fullStr Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes
title_full_unstemmed Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes
title_sort constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem heck/carbonylation desymmetrization of cyclopentenes
publisher Nature Publishing Group
series Nature Communications
issn 2041-1723
publishDate 2020-05-01
description 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.
url https://doi.org/10.1038/s41467-020-16221-9
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AT yuyezeng constructingchiralbicyclo321octanesviapalladiumcatalyzedasymmetrictandemheckcarbonylationdesymmetrizationofcyclopentenes
AT ziwenfeng constructingchiralbicyclo321octanesviapalladiumcatalyzedasymmetrictandemheckcarbonylationdesymmetrizationofcyclopentenes
AT zheguan constructingchiralbicyclo321octanesviapalladiumcatalyzedasymmetrictandemheckcarbonylationdesymmetrizationofcyclopentenes
AT aijunlin constructingchiralbicyclo321octanesviapalladiumcatalyzedasymmetrictandemheckcarbonylationdesymmetrizationofcyclopentenes
AT hequanyao constructingchiralbicyclo321octanesviapalladiumcatalyzedasymmetrictandemheckcarbonylationdesymmetrizationofcyclopentenes
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