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Water as the reaction medium for multicomponent reactions based on boronic acids

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Details

Original languageEnglish
Pages (from-to)2736-2745
Number of pages10
JournalTetrahedron
Volume66
Issue number14
DOIs
Publication statusPublished - 3 Apr 2010
Externally publishedYes
Publication typeA1 Journal article-refereed

Abstract

Water is a suitable medium for the Petasis-borono-Mannich multicomponent reaction Salicylaldehyde, glyoxalic acid, glycoaldehyde and glyoxal were reacted with several boronic acids and different amines affording alkylaminophenols, 2H-chromenes, alpha-amino acids, alpha-amino alcohols and 2-hydroxylmorpholines in good to high yields An efficient new one-pot method for the assembly of boron-heterocycles based on amino-acids, boronic acids and salicylaldehyde using water as the reaction media is presented The mechanisms of these reactions were studied by means of OFF calculations, and the effect of solvent on the calculated energy barriers was addressed, for different aldehydes (C) 2010 Elsevier Ltd All rights reserved

Keywords

  • Boron, Multicomponent reactions, Petasis reaction, Boron heterocycles, MOLECULAR-ORBITAL METHODS, DIELS-ALDER REACTIONS, POLARIZABLE CONTINUUM MODEL, GAUSSIAN-TYPE BASIS, ALPHA-AMINO-ACIDS, ORGANIC-REACTIONS, EQUILIBRIUM GEOMETRIES, TRANSITION-STATES, MANNICH REACTIONS, SOLVATION MODELS

Field of science, Statistics Finland