Synthesis of amino alcohols through one-popt catalytic boron addition sequences

Identifier:  TDX:1255

Handle: https://hdl.handle.net/20.500.11797/TDX1255

Authors:  Solé Marcé, Cristina

Abstract:
Amino alcohols are important building blocks extensively employed for the synthesis of natural products, pharmaceuticals, and for the production of chiral auxiliaries or catalysts used in asymmetric synthesis. Organoboranes can be utilized as interesting intermediates in organic chemistry. Taking into consideration the advantages of organoboronic esters and the importance of amino alcohols, four new one-pot routes to synthesize β– or γ–amino alcohols have been developed in this thesis. The first and the second were based on the catalytic β–boration of α,β–unsaturated imines followed by reduction of the corresponding imines and oxidation of C-B bond to obtain the desired γ–amino alcohol structure. The third was based on the organocatalytic β–amination of α,β–unsaturated ketones followed by the reduction of the C=O double bond. The last route was developed to synthesize β–amino alcohol, based on the enantioselective organocatalytic boryl addition to tosylaldimines followed by homologation/oxidation sequence.