Regio- and Diastereoselective Construction of Spirocyclopenteneoxindoles through Phosphine-Catalyzed [3 + 2] Annulation of Methyleneindolinone with Alkynoate Derivatives

Jiayong Zhang; Cheng Cheng; Dian Wang; Zhiwei Miao

doi:10.1021/acs.joc.7b01582

Regio- and Diastereoselective Construction of Spirocyclopenteneoxindoles through Phosphine-Catalyzed [3 + 2] Annulation of Methyleneindolinone with Alkynoate Derivatives

J Org Chem. 2017 Oct 6;82(19):10121-10128. doi: 10.1021/acs.joc.7b01582. Epub 2017 Sep 21.

Authors

Jiayong Zhang¹, Cheng Cheng¹, Dian Wang¹, Zhiwei Miao^{1

2}

Affiliations

¹ State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University , Weijin Road 94, Tianjin 300071, China.
² Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300071, China.

PMID: 28898577
DOI: 10.1021/acs.joc.7b01582

Abstract

A phosphine-catalyzed [3 + 2] annulation of isatin-derived α,β-unsaturated ketones with alkynoates for the synthesis of cyclopentene spiro-oxindole skeletons has been developed. This reaction afforded the desired products in high to excellent yields (up to 99%) with high regioselectivity and moderate to high diastereoselectivities (up to 20:1). This strategy allows facile diastereoselective preparation of biologically important spiro-(cyclopentene) oxindoles containing three contiguous stereocenters, including the quaternary stereogenic center joining the two rings.

Publication types

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