Highly enantioselective and organocatalytic alpha-amination of 2-oxindoles

Liang Cheng; Li Liu; Dong Wang; Yong-Jun Chen

doi:10.1021/ol901405r

Highly enantioselective and organocatalytic alpha-amination of 2-oxindoles

Org Lett. 2009 Sep 3;11(17):3874-7. doi: 10.1021/ol901405r.

Authors

Liang Cheng¹, Li Liu, Dong Wang, Yong-Jun Chen

Affiliation

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.

PMID: 19708700
DOI: 10.1021/ol901405r

Abstract

An effective method for the asymmetric synthesis of 3-amino-2-oxindoles was developed. The tetrasubstituted chiral carbon center was generated by asymmetric amination of N-unprotected 2-oxindoles with azodicarboxylate catalyzed by commercial biscinchona alkaloids in good to excellent yields with high enantioselectivities.

Publication types

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

MeSH terms

Amination
Catalysis
Indoles / chemical synthesis*
Indoles / chemistry*
Molecular Structure
Oxindoles
Stereoisomerism

Substances

Indoles
Oxindoles
2-oxindole