Synthesis of gem-difluorinated compounds via fluoroallylboration and preparation of amines and gamma-aminobutyric acids via reductive amination
Abstract
Reported herein is the application of fluoroallylboration for the synthesis of gem-difluorinated compounds. Allylboration is one of the most valuable methodologies available to synthetic chemists and the resulting homoallylic alcohols have served as versatile intermediates in synthetic organic chemistry. The introduction of fluorine has become a widespread and important component of organic chemistry and has led to remarkable advances in the pharmaceutical and agriculture industry. Using Ramachandran’s achiral difluoroallylborate, several gem-difluorinated homoallylic alcohols have been prepared and have been utilized in the synthesis of gem-difluorinated α-β-Unsaturated δ-lactones and preparation of gem-difluorinated nucleosides. A novel asymmetric difluoroallylborate has been developed and chiral gem-difluorinated homoallylic alcohols and δ-lactones have been prepared. The preparation of amines and γ- aminobutyric acid derivatives (GABA) via reductive amination employing ammonia borane has also been described.
Degree
Ph.D.
Advisors
Ramachandran, Purdue University.
Subject Area
Organic chemistry
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