Bis-exo-2-norbornylboron triflate for stereospecific enolization of 3,3,3-trifluoropropionates

P Veeraraghavan Ramachandran; Gowrisankar Parthasarathy; Pravin D Gagare

doi:10.1021/ol1016178

Bis-exo-2-norbornylboron triflate for stereospecific enolization of 3,3,3-trifluoropropionates

Org Lett. 2010 Oct 15;12(20):4474-7. doi: 10.1021/ol1016178.

Authors

P Veeraraghavan Ramachandran¹, Gowrisankar Parthasarathy, Pravin D Gagare

Affiliation

¹ Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA. [email protected]

PMID: 20849128
DOI: 10.1021/ol1016178

Abstract

The first boron-mediated enolization-aldolization of 3,3,3-trifluoropropionates has been reported. The preparation and application of bis-exo-bicyclo[2.2.1]heptan-2-ylboron triflate as a superior reagent for diastereospecific enolization has also been described.

Publication types

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

MeSH terms

Fluorine Compounds / chemical synthesis*
Methyldopa / chemistry
Molecular Structure
Norbornanes / chemical synthesis*
Propionates / chemical synthesis*
Stereoisomerism

Substances

Fluorine Compounds
Norbornanes
Propionates
2-norbornene
Methyldopa