Asymmetric Organocatalytic Wittig [2,3]-Rearrangement of Oxindoles

Maksim Ošeka; Mariliis Kimm; Sandra Kaabel; Ivar Järving; Kari Rissanen; Tõnis Kanger

doi:10.1021/acs.orglett.6b00291

Asymmetric Organocatalytic Wittig [2,3]-Rearrangement of Oxindoles

Org Lett. 2016 Mar 18;18(6):1358-61. doi: 10.1021/acs.orglett.6b00291. Epub 2016 Mar 3.

Authors

Maksim Ošeka¹, Mariliis Kimm¹, Sandra Kaabel^{1

2}, Ivar Järving¹, Kari Rissanen², Tõnis Kanger¹

Affiliations

¹ Department of Chemistry, Tallinn University of Technology , Akadeemia tee 15, 12618 Tallinn, Estonia.
² University of Jyvaskyla , Department of Chemistry, Nanoscience Center, P.O. Box 35, FI-40014 Jyvaskyla, Finland.

PMID: 26937554
DOI: 10.1021/acs.orglett.6b00291

Abstract

A highly enantioselective organocatalytic [2,3]-rearrangement of oxindole derivatives is presented. The reaction was catalyzed by squaramide, and this provides access to 3-hydroxy 3-substituted oxindoles in high enantiomeric purities.

Publication types

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

MeSH terms

Amides / chemistry
Catalysis
Combinatorial Chemistry Techniques
Indoles / chemical synthesis*
Indoles / chemistry
Molecular Structure
Oxindoles
Stereoisomerism

Substances

Amides
Indoles
Oxindoles
2-oxindole