Assembly of spirooxindole derivatives via organocatalytic iminium-enamine cascade reactions

Klaus Albertshofer; Kimberly E Anderson; Carlos F Barbas 3rd

doi:10.1021/ol302876c

Assembly of spirooxindole derivatives via organocatalytic iminium-enamine cascade reactions

Org Lett. 2012 Dec 7;14(23):5968-71. doi: 10.1021/ol302876c. Epub 2012 Nov 14.

Authors

Klaus Albertshofer¹, Kimberly E Anderson, Carlos F Barbas 3rd

Affiliation

¹ The Skaggs Institute for Chemical Biology and the Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

PMID: 23151228
DOI: 10.1021/ol302876c

Abstract

The assembly of complex spirocyclopentaneoxindoles via a novel organocatalytic iminium-enamine cascade process is reported. Reactions between 3-substituted oxindoles and α,β-unsaturated aldehydes catalyzed by second generation prolinol ethers provided the desired products in high yield with excellent levels of enantioselectivity in a single step.

Publication types

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

MeSH terms

Aldehydes / chemistry*
Catalysis
Combinatorial Chemistry Techniques
Ethers / chemistry
Heterocyclic Compounds, 3-Ring / chemical synthesis*
Heterocyclic Compounds, 3-Ring / chemistry
Indoles / chemistry*
Molecular Structure
Oxindoles
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Stereoisomerism

Substances

Aldehydes
Ethers
Heterocyclic Compounds, 3-Ring
Indoles
Oxindoles
Spiro Compounds
2-oxindole