Homologation of boronic esters with lithiated epoxides for the stereocontrolled synthesis of 1,2- and 1,3-diols and 1,2,4-triols

Emeline Vedrenne; Olov A Wallner; Maxime Vitale; Frank Schmidt; Varinder K Aggarwal

doi:10.1021/ol802651b

Homologation of boronic esters with lithiated epoxides for the stereocontrolled synthesis of 1,2- and 1,3-diols and 1,2,4-triols

Org Lett. 2009 Jan 1;11(1):165-8. doi: 10.1021/ol802651b.

Authors

Emeline Vedrenne¹, Olov A Wallner, Maxime Vitale, Frank Schmidt, Varinder K Aggarwal

Affiliation

¹ School of Chemistry, University of Bristol, Bristol BS81TS, UK.

PMID: 19067552
DOI: 10.1021/ol802651b

Abstract

Lithiated epoxides react stereospecifically with boronic esters to give syn-1,2-diols, a process that can be used iteratively to create triols containing four stereogenic centers.

MeSH terms

Alcohols / chemical synthesis*
Alcohols / chemistry
Boronic Acids / chemistry*
Epoxy Compounds / chemistry*
Esters / chemistry*
Lithium / chemistry*
Molecular Structure
Organometallic Compounds / chemistry*
Stereoisomerism

Substances

Alcohols
Boronic Acids
Epoxy Compounds
Esters
Organometallic Compounds
Lithium