Elsevier, Tetrahedron Letters, 46(44), p. 8369-8372, 2003
DOI: 10.1016/j.tetlet.2003.09.124
Wiley-VCH Verlag, ChemInform, 8(35), 2004
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Arylglycidols and their corresponding ethers undergo regioselective ring-opening with aqueous ammonia in the presence of organic co-solvents (isopropanol or 1,4-dioxane) to afford 1,2-amino alcohols in high yield. Chiral enantiopure amino alcohols are attractive com-pounds, either as ligands for asymmetric catalysis 1 or as building blocks for the preparation of biologically active molecules. 2 Among them, those bearing a free amino group present the opportunity of employing different protecting group strategies (e.g. N-Boc or N-F-moc), in the synthesis of biomolecules or, when dedicated to catalysis to being the starting materials for the preparation of important types of catalytic ligands such as oxazaborolidines, 3 bis(oxazolines), 4 or phosphinooxazolines. 5 A very common method for preparing N-unprotected 1,2-amino alcohols has been the addition of organometallic species onto the carboxyl group of natu-ral amino acids. 6 This method, however, provides only access to a limited set of amino alcohol structures. To overcome this limitation, we have developed methods for the stereospecific synthesis of enantiomerically pure b-amino alcohols (3, 4) through the regioselective and stereospecific ring opening of epoxyalcohols (1) or epoxyethers (2) arising from the Sharpless 7 epoxidation.