Catalytic asymmetric synthesis of spirooxindoles by a mannich-type reaction of isothiocyanato oxindoles

Shota Kato; Tatsuhiko Yoshino; Masakatsu Shibasaki; Motomu Kanai; Shigeki Matsunaga

doi:10.1002/anie.201203005

Catalytic asymmetric synthesis of spirooxindoles by a mannich-type reaction of isothiocyanato oxindoles

Angew Chem Int Ed Engl. 2012 Jul 9;51(28):7007-10. doi: 10.1002/anie.201203005. Epub 2012 Jun 4.

Authors

Shota Kato¹, Tatsuhiko Yoshino, Masakatsu Shibasaki, Motomu Kanai, Shigeki Matsunaga

Affiliation

¹ Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Japan.

PMID: 22674857
DOI: 10.1002/anie.201203005

Abstract

Easy access: a strontium/Schiff base complex as catalyst for the title reaction provided straightforward access to enantiomerically enriched spiro[imidazolidine-4,3'-oxindole] compounds, as well as a spiro[imidazoline-4,3'-oxindole] through a two-step conversion from the Mannich adduct.

Publication types

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

MeSH terms

Catalysis
Indoles / chemical synthesis*
Isothiocyanates / chemistry*
Mannich Bases / chemistry*
Molecular Structure
Oxindoles
Schiff Bases / chemistry*
Spiro Compounds / chemical synthesis*
Stereoisomerism

Substances

Indoles
Isothiocyanates
Mannich Bases
Oxindoles
Schiff Bases
Spiro Compounds
2-oxindole