Fluoroallylboration-olefination for the synthesis of (Z)-4,4-difluoropent-2-enoates and 5,5-difluoro-5,6-dihydropyran-2-ones

P Veeraraghavan Ramachandran; Agnieszka Tafelska-Kaczmarek; Kaumba Sakavuyi; Anamitra Chatterjee

doi:10.1021/ol103097s

Fluoroallylboration-olefination for the synthesis of (Z)-4,4-difluoropent-2-enoates and 5,5-difluoro-5,6-dihydropyran-2-ones

Org Lett. 2011 Mar 18;13(6):1302-5. doi: 10.1021/ol103097s. Epub 2011 Feb 18.

Authors

P Veeraraghavan Ramachandran¹, Agnieszka Tafelska-Kaczmarek, Kaumba Sakavuyi, Anamitra Chatterjee

Affiliation

¹ Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, United States. chandran@purdue.edu

PMID: 21332156
DOI: 10.1021/ol103097s

Abstract

Horner-Wadsworth-Emmons (HWE) or Still-Gennari olefination of TBS-protected 3,3-difluoro-4-hydroxy-2-ones, derived from the difluoroallylboration of aldehydes, provides the Z-isomer of 4,4,-difluoropent-2-enoates. These, upon hydrolysis, followed by Yamaguchi cyclization, afford 5,5-difluoro-4-methyl-5,6-dihydro-α-pyrones in high yields.

Publication types

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

MeSH terms

Aldehydes / chemistry*
Alkenes / chemical synthesis*
Alkenes / chemistry
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Hydrocarbons, Fluorinated / chemical synthesis*
Hydrocarbons, Fluorinated / chemistry
Molecular Structure
Pyrones / chemical synthesis*
Pyrones / chemistry
Stereoisomerism

Substances

Aldehydes
Alkenes
Hydrocarbons, Fluorinated
Pyrones