Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones

Zhanglin Shi; Chaoren Shen; Kaiwu Dong

doi:10.1002/chem.202103318

Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones

Zhanglin Shi, Chaoren Shen, Kaiwu Dong^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.

Original language	English
Pages (from-to)	18039-18042
Number of pages	4
Journal	Chemistry - A European Journal
Volume	27
Issue number	72
DOIs	https://doi.org/10.1002/chem.202103318
State	Published - 23 Dec 2021

Keywords

alkene
diastereoselective carbonylation
hydroxyl group
palladium
γ-lactone

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10.1002/chem.202103318

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title = "Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones",

abstract = "Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.",

keywords = "alkene, diastereoselective carbonylation, hydroxyl group, palladium, γ-lactone",

author = "Zhanglin Shi and Chaoren Shen and Kaiwu Dong",

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year = "2021",

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T1 - Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones

AU - Shi, Zhanglin

AU - Shen, Chaoren

AU - Dong, Kaiwu

PY - 2021/12/23

Y1 - 2021/12/23

N2 - Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.

AB - Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.

KW - alkene

KW - diastereoselective carbonylation

KW - hydroxyl group

KW - palladium

KW - γ-lactone

UR - https://www.scopus.com/pages/publications/85118849223

U2 - 10.1002/chem.202103318

DO - 10.1002/chem.202103318

M3 - 文章

C2 - 34734440

AN - SCOPUS:85118849223

SN - 0947-6539

VL - 27

SP - 18039

EP - 18042

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 72

ER -

Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones

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Keywords

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