Preparation and reactions of stable aldimine-borane complexes. Synthesis of GABA analogs, β-lactams, and δ-aminoboronic esters. Electrophysiological screening of GABA analogs
Abstract
Reported herein is the synthesis of a novel class of stable aldimine-trialkylborane complexes, including C- and N-deuterated imine-borane complexes, from nitriles. Allylboration, crotylboration, and alkoxyallylboration of these imine-borane complexes provide a convenient access to the preparation of a class of diversely functionalized homoallylic amines. Using this protocol, aryl dinitriles have been converted to C2-symmetric bis-homoallylic diamines. Preparation of lithium B-allyldiisopinocampheylborohydride and it application for the tandem reduction-allylboration of nitriles and the allylboration of aldehydes has been investigated. Synthesis of new γ-substituted γ-aminobutyric acid analogs, δ-aminoboronic esters, and β-lactams starting from nitriles has been reported. Patch-clamp electrophysiological screening of selected γ-substituted GABA analogs as potential agonists of GABA-A receptors has also been described.
Degree
Ph.D.
Advisors
Ramachandran, Purdue University.
Subject Area
Organic chemistry
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