Synthesis 2022; 54(03): 779-787
DOI: 10.1055/a-1588-0974
paper

Ruthenium-Catalyzed Alkylation of Cyclopropanols with Sulfoxonium Ylides via C–C Bond Cleavage: Formation of Diverse 1,5-Diketones

Xin Huang
a   West China Hospital, Sichuan University, Chengdu, 610041, P. R. of China
b   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China
,
Jianglian Li
b   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China
,
Hua He
b   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China
,
Kaichuan Yan
b   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China
,
Ruizhi Lai
b   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China
,
Yi Luo
b   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China
,
Mei Guan
a   West China Hospital, Sichuan University, Chengdu, 610041, P. R. of China
,
Yong Wu
b   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China
› Author Affiliations
This work was supported by the National Natural Science Foundation of China (81573286 and 81373259).


Abstract

A novel ruthenium-catalyzed alkylation of cyclopropanols with sulfoxonium ylides has been developed that affords diverse 1,5-diketones with good efficiency and broad substrate scope. To illustrate the synthetic applications of the obtained 1,5-diketones, aldol and cyclization reactions have been investigated. Preliminary mechanistic studies suggest that this process involves a sequential C–C activation and carbene migratory insertion.

Supporting Information



Publication History

Received: 08 July 2021

Accepted after revision: 16 August 2021

Accepted Manuscript online:
16 August 2021

Article published online:
18 October 2021

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