Lewis base activation of Lewis acids: development of a Lewis base catalyzed selenolactonization

Scott E Denmark; William R Collins

doi:10.1021/ol701617d

Lewis base activation of Lewis acids: development of a Lewis base catalyzed selenolactonization

Org Lett. 2007 Sep 13;9(19):3801-4. doi: 10.1021/ol701617d. Epub 2007 Aug 17.

Authors

Scott E Denmark¹, William R Collins

Affiliation

¹ Roger Adams Laboratory, Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu

PMID: 17705396
DOI: 10.1021/ol701617d

Abstract

The concept of Lewis base activation of Lewis acids has been applied to the selenolactonization reaction. Through the use of substoichiometric amounts of Lewis bases with "soft" donor atoms (S, Se, P) significant rate enhancements over the background reaction are seen. Preliminary mechanistic investigations have revealed the resting state of the catalyst as well as the significance of a weak Brønsted acid promoter.

Publication types

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

MeSH terms

Acids / chemistry*
Alkalies / chemistry*
Carboxylic Acids / chemistry
Catalysis
Electrons
Hydrogen-Ion Concentration
Lactones / chemical synthesis
Lactones / chemistry*
Molecular Structure
Protons
Selenium Compounds / chemical synthesis*
Selenium Compounds / chemistry

Substances

Acids
Alkalies
Carboxylic Acids
Lactones
Protons
Selenium Compounds