Rhodium-Catalyzed Regioselective Formal Hydroacylation of Vinyl Epoxides toward Esters Involving β-Carbon Cleavage

Zhi-Xin Chang; Fei-Yuan Gong; Xiaodan Wang; Tongbo Zhang; Junfen Han; Hong-Shuang Li

doi:10.1021/acs.orglett.1c02153

Rhodium-Catalyzed Regioselective Formal Hydroacylation of Vinyl Epoxides toward Esters Involving β-Carbon Cleavage

Org Lett. 2021 Aug 6;23(15):6084-6089. doi: 10.1021/acs.orglett.1c02153. Epub 2021 Jul 21.

Authors

Zhi-Xin Chang¹, Fei-Yuan Gong¹, Xiaodan Wang¹, Tongbo Zhang², Junfen Han¹, Hong-Shuang Li¹

Affiliations

¹ Institute of Pharmacology, School of Pharmaceutical Sciences, Shandong First Medical University & Shandong Academy of Medical Sciences, Taian 271016, P. R. China.
² Beijing Pharmaceutical Research Institute, Heilongjiang ZBD Pharmaceutical Co., Ltd., Beijing 101102, P. R. China.

PMID: 34286983
DOI: 10.1021/acs.orglett.1c02153

Abstract

Herein we disclose the first example of the formal hydroacylation reactions of vinyl epoxides with chelating aldehydes enabled by rhodium catalysis for the efficient construction of functionalized esters. Detailed investigations of the mechanistic pathway reveal that the presence of a 2-vinyl group is essential in contributing to the success of this regioselective reaction, which might proceed through β-carbon cleavage as the key procedure.