Stereoselective synthesis of 1,3-disubstituted isoindolines via Rh(III)-catalyzed tandem oxidative olefination-cyclization of 4-aryl cyclic sulfamidates

Se-Mi Son; Yeon Ji Seo; Hyeon-Kyu Lee

doi:10.1039/c5cc09888b

Stereoselective synthesis of 1,3-disubstituted isoindolines via Rh(III)-catalyzed tandem oxidative olefination-cyclization of 4-aryl cyclic sulfamidates

Chem Commun (Camb). 2016 Mar 21;52(23):4286-9. doi: 10.1039/c5cc09888b.

Authors

Se-Mi Son¹, Yeon Ji Seo², Hyeon-Kyu Lee²

Affiliations

¹ Korea Chemical Bank, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Korea. leehk@krict.re.kr.
² Korea Chemical Bank, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Korea. leehk@krict.re.kr and Department of Medicinal Chemistry and Pharmacology, University of Science and Technology, 113 Gwahango, Yuseong, Daejeon 305-333, Korea.

PMID: 26841961
DOI: 10.1039/c5cc09888b

Abstract

Rh(III)-catalyzed tandem ortho C-H olefination of cyclic 4-aryl sulfamidates (1) and subsequent intramolecular cyclization are described. This reaction serves as a method for the direct and stereoselective synthesis of 1,3-disubstituted isoindolines (3) starting with enantiomerically enriched 4-aryl cyclic sulfamidates. In this process, the configurational integrity of the stereogenic center in the starting cyclic sulfamidate is completely retained. In addition, the process generates trans-1,3-disubstituted isoindolines exclusively.

Publication types

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