Cascade oxidative dearomatization/semipinacol rearrangement: an approach to 2-spirocyclo-3-oxindole derivatives

Jin-Bao Peng; Yue Qi; Ai-Jun Ma; Yong-Qiang Tu; Fu-Min Zhang; Shao-Hua Wang; Shu-Yu Zhang

doi:10.1002/asia.201300032

Cascade oxidative dearomatization/semipinacol rearrangement: an approach to 2-spirocyclo-3-oxindole derivatives

Chem Asian J. 2013 May;8(5):883-7. doi: 10.1002/asia.201300032. Epub 2013 Feb 19.

Authors

Jin-Bao Peng¹, Yue Qi, Ai-Jun Ma, Yong-Qiang Tu, Fu-Min Zhang, Shao-Hua Wang, Shu-Yu Zhang

Affiliation

¹ State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P R China.

PMID: 23423783
DOI: 10.1002/asia.201300032

Abstract

A novel cascade reaction involving oxidative dearomatization/semipinacol rearrangement of indol-2-yl cyclobutanols is explored with N-sulfonyloxaziridine (Davis oxaziridines) as oxidant, generating various 2-spiroquaternary 3-oxindoles in modest to good yields. This method might be useful in the synthesis of indole-based alkaloids bearing 2-spiroquaternary carbon centers. PTS=p-toluenesulfonic acid monohydrate.

Publication types

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

MeSH terms

Aziridines / chemistry*
Crystallography, X-Ray
Cyclobutanes / chemistry*
Indoles / chemical synthesis*
Indoles / chemistry
Models, Molecular
Molecular Structure
Oxidation-Reduction
Oxindoles
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry

Substances

Aziridines
Cyclobutanes
Indoles
Oxindoles
Spiro Compounds
2-oxindole