FeCl3-Mediated Radical Tandem Reactions of 3-Benzyl-2-oxindoles with Styrene Derivatives for the Stereoselective Synthesis of Spirocyclohexene Oxindoles

Hong-Ru Wu; Liang Cheng; De-Long Kong; Hong-Yan Huang; Chun-Ling Gu; Li Liu; Dong Wang; Chao-Jun Li

doi:10.1021/acs.orglett.6b00234

FeCl3-Mediated Radical Tandem Reactions of 3-Benzyl-2-oxindoles with Styrene Derivatives for the Stereoselective Synthesis of Spirocyclohexene Oxindoles

Org Lett. 2016 Mar 18;18(6):1382-5. doi: 10.1021/acs.orglett.6b00234. Epub 2016 Mar 7.

Authors

Hong-Ru Wu^{1

2}, Liang Cheng¹, De-Long Kong^{1

2}, Hong-Yan Huang^{1

2}, Chun-Ling Gu¹, Li Liu¹, Dong Wang¹, Chao-Jun Li³

Affiliations

¹ Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190, China.
² University of Chinese Academy of Sciences , Beijing 100049, China.
³ Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.

PMID: 26950164
DOI: 10.1021/acs.orglett.6b00234

Abstract

A novel FeCl3-mediated reaction of 3-benzyl-2-oxindoles with styrene derivatives was developed. The reaction provided spirocyclohexene oxindoles in good yields and excellent diastereoselectivities via a tandem radical addition/cyclization process.

Publication types

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

MeSH terms

Catalysis
Chlorides / chemistry*
Cyclization
Cyclohexenes / chemical synthesis*
Cyclohexenes / chemistry
Ferric Compounds / chemistry*
Indoles / chemical synthesis*
Indoles / chemistry
Molecular Structure
Oxindoles
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Stereoisomerism
Styrenes / chemistry*

Substances

Chlorides
Cyclohexenes
Ferric Compounds
Indoles
Oxindoles
Spiro Compounds
Styrenes
2-oxindole
cyclohexene
ferric chloride