Efficient Synthesis of γ-Lactones by Cobalt-Catalyzed Carbonylative Ring Expansion of Oxetanes under Syngas Atmosphere

Yitian Tang; Chaoren Shen; Qiyi Yao; Xinxin Tian; Bo Wang; Kaiwu Dong

doi:10.1002/cctc.202001294

Efficient Synthesis of γ-Lactones by Cobalt-Catalyzed Carbonylative Ring Expansion of Oxetanes under Syngas Atmosphere

Yitian Tang
, Chaoren Shen
, Qiyi Yao
, Xinxin Tian
, Bo Wang
, Kaiwu Dong^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

15 Scopus citations

Abstract

A practical route from oxetane or thietane to γ-(thio)butyrolactone via solvated-proton-assisted cobalt-catalyzed carbonylative ring expansion under syngas atmosphere has been established. A wide variety of γ-(thio)butyrolactones can be afforded in good to excellent yields. The versatility of this method has been well demonstrated in the synthesis of intermediates towards the natural product Arctigenin as well as the pharmaceuticals Baclofen and Montelukast. The observed promoting effect of glycol ether solvent has been rationally interpreted.

Original language	English
Pages (from-to)	5898-5902
Number of pages	5
Journal	ChemCatChem
Volume	12
Issue number	23
DOIs	https://doi.org/10.1002/cctc.202001294
State	Published - 4 Dec 2020

Keywords

carbonylation
oxetane
ring expansion
solvent effect
γ-butyrolactone

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10.1002/cctc.202001294

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title = "Efficient Synthesis of γ-Lactones by Cobalt-Catalyzed Carbonylative Ring Expansion of Oxetanes under Syngas Atmosphere",

abstract = "A practical route from oxetane or thietane to γ-(thio)butyrolactone via solvated-proton-assisted cobalt-catalyzed carbonylative ring expansion under syngas atmosphere has been established. A wide variety of γ-(thio)butyrolactones can be afforded in good to excellent yields. The versatility of this method has been well demonstrated in the synthesis of intermediates towards the natural product Arctigenin as well as the pharmaceuticals Baclofen and Montelukast. The observed promoting effect of glycol ether solvent has been rationally interpreted.",

keywords = "carbonylation, oxetane, ring expansion, solvent effect, γ-butyrolactone",

author = "Yitian Tang and Chaoren Shen and Qiyi Yao and Xinxin Tian and Bo Wang and Kaiwu Dong",

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T1 - Efficient Synthesis of γ-Lactones by Cobalt-Catalyzed Carbonylative Ring Expansion of Oxetanes under Syngas Atmosphere

AU - Tang, Yitian

AU - Shen, Chaoren

AU - Yao, Qiyi

AU - Tian, Xinxin

AU - Wang, Bo

AU - Dong, Kaiwu

PY - 2020/12/4

Y1 - 2020/12/4

N2 - A practical route from oxetane or thietane to γ-(thio)butyrolactone via solvated-proton-assisted cobalt-catalyzed carbonylative ring expansion under syngas atmosphere has been established. A wide variety of γ-(thio)butyrolactones can be afforded in good to excellent yields. The versatility of this method has been well demonstrated in the synthesis of intermediates towards the natural product Arctigenin as well as the pharmaceuticals Baclofen and Montelukast. The observed promoting effect of glycol ether solvent has been rationally interpreted.

AB - A practical route from oxetane or thietane to γ-(thio)butyrolactone via solvated-proton-assisted cobalt-catalyzed carbonylative ring expansion under syngas atmosphere has been established. A wide variety of γ-(thio)butyrolactones can be afforded in good to excellent yields. The versatility of this method has been well demonstrated in the synthesis of intermediates towards the natural product Arctigenin as well as the pharmaceuticals Baclofen and Montelukast. The observed promoting effect of glycol ether solvent has been rationally interpreted.

KW - carbonylation

KW - oxetane

KW - ring expansion

KW - solvent effect

KW - γ-butyrolactone

UR - https://www.scopus.com/pages/publications/85091686576

U2 - 10.1002/cctc.202001294

DO - 10.1002/cctc.202001294

M3 - 文章

AN - SCOPUS:85091686576

SN - 1867-3880

VL - 12

SP - 5898

EP - 5902

JO - ChemCatChem

JF - ChemCatChem

IS - 23

ER -

Efficient Synthesis of γ-Lactones by Cobalt-Catalyzed Carbonylative Ring Expansion of Oxetanes under Syngas Atmosphere

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Keywords

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