Bromo-boronolactonization of olefins

J R Falck; M Bondlela; S K Venkataraman; D Srinivas

doi:10.1021/jo015838z

Bromo-boronolactonization of olefins

J Org Chem. 2001 Oct 19;66(21):7148-50. doi: 10.1021/jo015838z.

Authors

J R Falck¹, M Bondlela, S K Venkataraman, D Srinivas

Affiliation

¹ Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, Texas 75390-9038, USA. j.flack@utsouthwestern.edu

PMID: 11597243
DOI: 10.1021/jo015838z

Abstract

Exposure of a variety of mono- and disubstituted ortho-alkenylarylboronic acids to NBS in THF/H(2)O under neutral conditions affords bromo-boronolactones, in some instances, with exceptional regiocontrol. The adducts, analogous to those formed by carboxylic acids, are shown to be useful synthetic intermediates.

Publication types

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

MeSH terms

Alkenes / chemistry
Boron Compounds / chemical synthesis*
Boron Compounds / chemistry
Boronic Acids / chemistry
Lactones / chemical synthesis*

Substances

Alkenes
Boron Compounds
Boronic Acids
Lactones

Grants and funding

GM 31278/GM/NIGMS NIH HHS/United States