| This thesis describes several new reactions of organoboronic acids and their applications to the facile stereocontrolled synthesis of halogenated compounds, allylamines, amino acids, 1,1'-iminodicarboxylic acids, and amino alcohol derivatives.; Chapter 1 of this thesis represents a review of the recent work on the synthesis and utilization of alkenylboron compounds. These boron derivatives are highly versatile synthetic intermediates and possess a number of beneficial properties compared to other organometallic reagents. The use of boronic acid derivatives is especially attractive since these compounds are readily available in geometrically pure form, are easy to handle and environmentally benign.; Chapter 2 first surveys currently available methods for the conversion of alkenylboronic acids into alkenyl halides. A new method for the synthesis of stereodefined alkenyl halides, 2,2-difluoro substituted alcohols and amines is then introduced using the reaction of alkenylboronic acids with halosuccinimides and electrophilic fluorinating reagents.; Chapter 3 details our studies of the mechanism and scope of the Boronic Acid Mannich (BAM) allylamine reaction. Successful preparation of several geometrically pure (Z)-allylamines confirmed the exceptionally high stereoselectivity of this process, while formaldehyde hemiaminals were found to be the most reactive species in the BAM reactions.; Chapters 4, 5, and 6 introduce a new version of BAM reaction which involves the one-pot three-component condensation between an organoboronic acid, an amine and an alpha-keto acid to give an alpha-amino acid derivative. This new multicomponent reaction has been successfully applied to the stereoselective synthesis of beta,gamma-unsaturated alpha-amino acids (Chapter 4), alpha-arylglycines (Chapter 5), and 1,1'-iminodicarboxylic acid derivatives (Chapter 6).; Chapter 7 describes a new version of BAM reaction which involves the one-pot three-component condensation between an organoboronic acid, an amine and a hydroxy carbonyl compound to give an amino alcohol derivative. The applications of this multicomponent reaction to the highly stereocontrolled synthesis of 2-amino alcohols, 3-amino-1,2-diol and 2-amino-1,3-propanediol derivatives, polyhydroxylated amines, amino sugars, and other amino alcohol derivatives are described. |
