Organocatalytic Cloke-Wilson Rearrangement: DABCO-Catalyzed Ring Expansion of Cyclopropyl Ketones to 2,3-Dihydrofurans

Jingfang Zhang; Yuhai Tang; Wen Wei; Yong Wu; Yang Li; Junjie Zhang; Yuansuo Zheng; Silong Xu

doi:10.1021/acs.orglett.7b00805

Organocatalytic Cloke-Wilson Rearrangement: DABCO-Catalyzed Ring Expansion of Cyclopropyl Ketones to 2,3-Dihydrofurans

Jingfang Zhang
, Yuhai Tang
, Wen Wei
, Yong Wu
, Yang Li
, Junjie Zhang
, Yuansuo Zheng
, Silong Xu

化学学院

Xi'an Jiaotong University

科研成果: 期刊稿件 › 文章 › 同行评审

91 引用（Scopus）

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An organocatalytic Cloke-Wilson rearrangement of cyclopropyl ketones to 2,3-dihydrofurans is exploited utilizing the homoconjugate addition process. With 1,4-diazabicyclo[2.2.2]octane as the catalyst, the rearrangement in DMSO at 120 °C proceeded in generally high yields, exclusive regioselectivity, and a broad substrate scope. An examination of the mechanism including stereochemical analysis and intermediate isolation supports an S_N1-type ring opening of the mechanism.

源语言	英语
页（从-至）	3043-3046
页数	4
期刊	Organic Letters
卷	19
期	12
DOI	https://doi.org/10.1021/acs.orglett.7b00805
出版状态	已出版 - 16 6月 2017

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title = "Organocatalytic Cloke-Wilson Rearrangement: DABCO-Catalyzed Ring Expansion of Cyclopropyl Ketones to 2,3-Dihydrofurans",

abstract = "An organocatalytic Cloke-Wilson rearrangement of cyclopropyl ketones to 2,3-dihydrofurans is exploited utilizing the homoconjugate addition process. With 1,4-diazabicyclo[2.2.2]octane as the catalyst, the rearrangement in DMSO at 120 °C proceeded in generally high yields, exclusive regioselectivity, and a broad substrate scope. An examination of the mechanism including stereochemical analysis and intermediate isolation supports an SN1-type ring opening of the mechanism.",

author = "Jingfang Zhang and Yuhai Tang and Wen Wei and Yong Wu and Yang Li and Junjie Zhang and Yuansuo Zheng and Silong Xu",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

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doi = "10.1021/acs.orglett.7b00805",

language = "英语",

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T1 - Organocatalytic Cloke-Wilson Rearrangement

T2 - DABCO-Catalyzed Ring Expansion of Cyclopropyl Ketones to 2,3-Dihydrofurans

AU - Zhang, Jingfang

AU - Tang, Yuhai

AU - Wei, Wen

AU - Wu, Yong

AU - Li, Yang

AU - Zhang, Junjie

AU - Zheng, Yuansuo

AU - Xu, Silong

PY - 2017/6/16

Y1 - 2017/6/16

N2 - An organocatalytic Cloke-Wilson rearrangement of cyclopropyl ketones to 2,3-dihydrofurans is exploited utilizing the homoconjugate addition process. With 1,4-diazabicyclo[2.2.2]octane as the catalyst, the rearrangement in DMSO at 120 °C proceeded in generally high yields, exclusive regioselectivity, and a broad substrate scope. An examination of the mechanism including stereochemical analysis and intermediate isolation supports an SN1-type ring opening of the mechanism.

AB - An organocatalytic Cloke-Wilson rearrangement of cyclopropyl ketones to 2,3-dihydrofurans is exploited utilizing the homoconjugate addition process. With 1,4-diazabicyclo[2.2.2]octane as the catalyst, the rearrangement in DMSO at 120 °C proceeded in generally high yields, exclusive regioselectivity, and a broad substrate scope. An examination of the mechanism including stereochemical analysis and intermediate isolation supports an SN1-type ring opening of the mechanism.

UR - https://www.scopus.com/pages/publications/85020942539

U2 - 10.1021/acs.orglett.7b00805

DO - 10.1021/acs.orglett.7b00805

M3 - 文章

C2 - 28548502

AN - SCOPUS:85020942539

SN - 1523-7060

VL - 19

SP - 3043

EP - 3046

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Organocatalytic Cloke-Wilson Rearrangement: DABCO-Catalyzed Ring Expansion of Cyclopropyl Ketones to 2,3-Dihydrofurans

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