Construction of Vicinal Quaternary Carbon Centers via Cobalt-Catalyzed Asymmetric Reverse Prenylation

Minghe Sun; Jia-Feng Chen; Shufeng Chen; Changkun Li

doi:10.1021/acs.orglett.8b04030

Construction of Vicinal Quaternary Carbon Centers via Cobalt-Catalyzed Asymmetric Reverse Prenylation

Org Lett. 2019 Mar 1;21(5):1278-1282. doi: 10.1021/acs.orglett.8b04030. Epub 2019 Feb 15.

Authors

Minghe Sun¹, Jia-Feng Chen², Shufeng Chen¹, Changkun Li²

Affiliations

¹ Inner Mongolia Key Laboratory of Fine Organic Synthesis, Department of Chemistry and Chemical Engineering , Inner Mongolia University , Hohhot 010021 , People's Republic of China.
² Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering , Shanghai Jiao Tong University , 800 Dongchuan Road , Shanghai 200240 , People's Republic of China.

PMID: 30768277
DOI: 10.1021/acs.orglett.8b04030

Abstract

A highly enantioselective cobalt-catalyzed reverse prenylation of β-ketoester with tertiary allylic carbonate to construct vicinal all-carbon quaternary carbon centers has been developed. By using the cobalt/( S, S)Ph-BPE complex generated in situ with zinc reduction, excellent branched to linear selectivity (>20:1) and up to 92% ee have been obtained.

Publication types

Research Support, Non-U.S. Gov't