Isothiourea-mediated stereoselective C-acylation of silyl ketene acetals

Philip A Woods; Louis C Morrill; Tomas Lebl; Alexandra M Z Slawin; Ryan A Bragg; Andrew D Smith

doi:10.1021/ol1008747

Isothiourea-mediated stereoselective C-acylation of silyl ketene acetals

Org Lett. 2010 Jun 4;12(11):2660-3. doi: 10.1021/ol1008747.

Authors

Philip A Woods¹, Louis C Morrill, Tomas Lebl, Alexandra M Z Slawin, Ryan A Bragg, Andrew D Smith

Affiliation

¹ EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St. Andrews KY16 9ST, UK.

PMID: 20459078
DOI: 10.1021/ol1008747

Abstract

Isothiourea DHPB promotes the diastereoselective C-acylation of silyl ketene acetals with anhydrides or benzoyl fluoride, giving 3-acyl-3-aryl or 3-acyl-3-alkylfuranones in excellent yields and stereoselectivities (up to 99:1 dr).

Publication types

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

MeSH terms

Acetals / chemistry*
Acylation
Anhydrides / chemistry
Catalysis
Ethylenes / chemistry*
Furans / chemical synthesis*
Furans / chemistry
Ketones / chemistry*
Molecular Structure
Silanes / chemistry*
Stereoisomerism
Thiourea / chemistry*

Substances

Acetals
Anhydrides
Ethylenes
Furans
Ketones
Silanes
Thiourea
ketene