Diastereoselective Synthesis of Bicyclo[3.3.0]octenones by Copper-Catalyzed Transannular Ring-Closing Reaction

Qiongwen Kang; Yuanyang Mu; Yang Yuan; Ye Wang; Shuxin Jin; Chengyu Wang; Yanzhong Li

doi:10.1021/acs.orglett.2c02163

Diastereoselective Synthesis of Bicyclo[3.3.0]octenones by Copper-Catalyzed Transannular Ring-Closing Reaction

Qiongwen Kang, Yuanyang Mu, Yang Yuan, Ye Wang, Shuxin Jin, Chengyu Wang, Yanzhong Li

School of Chemistry and Molecular Engineering

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

3 Scopus citations

Abstract

A novel and efficient copper-catalyzed transannular ring-closing reaction of eight-membered rings has been developed that provides a straightforward way to synthesize bicyclo[3.3.0]octane derivatives in good yields. Mechanistic studies revealed that the reaction pathway might involve chlorination followed by the Kornblum reaction. Readily accessible starting materials and good functional group tolerance make this procedure attractive.

Original language	English
Pages (from-to)	5924-5928
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	32
DOIs	https://doi.org/10.1021/acs.orglett.2c02163
State	Published - 19 Aug 2022

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10.1021/acs.orglett.2c02163

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abstract = "A novel and efficient copper-catalyzed transannular ring-closing reaction of eight-membered rings has been developed that provides a straightforward way to synthesize bicyclo[3.3.0]octane derivatives in good yields. Mechanistic studies revealed that the reaction pathway might involve chlorination followed by the Kornblum reaction. Readily accessible starting materials and good functional group tolerance make this procedure attractive.",

author = "Qiongwen Kang and Yuanyang Mu and Yang Yuan and Ye Wang and Shuxin Jin and Chengyu Wang and Yanzhong Li",

year = "2022",

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journal = "Organic Letters",

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T1 - Diastereoselective Synthesis of Bicyclo[3.3.0]octenones by Copper-Catalyzed Transannular Ring-Closing Reaction

AU - Kang, Qiongwen

AU - Mu, Yuanyang

AU - Yuan, Yang

AU - Wang, Ye

AU - Jin, Shuxin

AU - Wang, Chengyu

AU - Li, Yanzhong

PY - 2022/8/19

Y1 - 2022/8/19

N2 - A novel and efficient copper-catalyzed transannular ring-closing reaction of eight-membered rings has been developed that provides a straightforward way to synthesize bicyclo[3.3.0]octane derivatives in good yields. Mechanistic studies revealed that the reaction pathway might involve chlorination followed by the Kornblum reaction. Readily accessible starting materials and good functional group tolerance make this procedure attractive.

AB - A novel and efficient copper-catalyzed transannular ring-closing reaction of eight-membered rings has been developed that provides a straightforward way to synthesize bicyclo[3.3.0]octane derivatives in good yields. Mechanistic studies revealed that the reaction pathway might involve chlorination followed by the Kornblum reaction. Readily accessible starting materials and good functional group tolerance make this procedure attractive.

UR - https://www.scopus.com/pages/publications/85136029930

U2 - 10.1021/acs.orglett.2c02163

DO - 10.1021/acs.orglett.2c02163

M3 - 文章

C2 - 35930708

AN - SCOPUS:85136029930

SN - 1523-7060

VL - 24

SP - 5924

EP - 5928

JO - Organic Letters

JF - Organic Letters

IS - 32

ER -

Diastereoselective Synthesis of Bicyclo[3.3.0]octenones by Copper-Catalyzed Transannular Ring-Closing Reaction

Abstract

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