Diastereospecific and Enantioselective Access to Dispirooxindoles from Furfurylcyclobutanols by Means of a Pd-Catalyzed Arylative Dearomatization/Ring Expansion Cascade

Jianchao Liu; Hui Peng; Lin Lu; Xiaobing Xu; Huanfeng Jiang; Biaolin Yin

doi:10.1021/acs.orglett.6b03339

Diastereospecific and Enantioselective Access to Dispirooxindoles from Furfurylcyclobutanols by Means of a Pd-Catalyzed Arylative Dearomatization/Ring Expansion Cascade

Org Lett. 2016 Dec 16;18(24):6440-6443. doi: 10.1021/acs.orglett.6b03339. Epub 2016 Dec 5.

Authors

Jianchao Liu¹, Hui Peng¹, Lin Lu¹, Xiaobing Xu¹, Huanfeng Jiang¹, Biaolin Yin¹

Affiliation

¹ Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology , Guangzhou 510640, P. R. China.

PMID: 27978697
DOI: 10.1021/acs.orglett.6b03339

Abstract

We report a Pd-catalyzed arylative dearomatization/ring expansion cascade of furfurylcyclobutanols that involves a spiro π-allyl palladium intermediate and affords structurally novel dispirooxindoles containing two quaternary carbon centers in good yields with high step economy, diastereospecificity, and enantioselectivity.

Publication types

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