Trapping of oxonium ylide with isatins: efficient and stereoselective construction of adjacent quaternary carbon centers

Xin Guo; Haoxi Huang; Liping Yang; Wenhao Hu

doi:10.1021/ol7019857

Trapping of oxonium ylide with isatins: efficient and stereoselective construction of adjacent quaternary carbon centers

Org Lett. 2007 Nov 8;9(23):4721-3. doi: 10.1021/ol7019857. Epub 2007 Oct 11.

Authors

Xin Guo¹, Haoxi Huang, Liping Yang, Wenhao Hu

Affiliation

¹ Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, P. R. China.

PMID: 17929823
DOI: 10.1021/ol7019857

Abstract

The 3-substituted 3-hydroxyindolin-2-ones with adjacent quaternary stereocenters were constructed in a single step via an efficient and stereoselective trapping of oxonium ylide with isatins. This reaction proceeds well in supercritical CO2 and is an example of the ability to use green approaches to efficiently construct polyfunctional molecules.

Publication types

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

MeSH terms

Aldehydes / chemistry
Carbon / chemistry*
Crystallography, X-Ray
Hydroxylation
Imines / chemistry
Isatin / chemistry*
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Oxazines / chemistry*
Peptides, Cyclic / chemistry
Stereoisomerism

Substances

Aldehydes
Imines
Oxazines
Peptides, Cyclic
TMC-95C
Carbon
Isatin