Journal
TETRAHEDRON
Volume 62, Issue 17, Pages 4027-4037Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.02.023
Keywords
2-hydroxymorpholine; multicomponent reaction; boro-Mannich condensation; boronic acid; chiral aminodiol
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The three-component coupling of an 1,2-aminoalcohol, a 1,2-dicarbonyl compound and a boronic acid was investigated. The reaction is supposed to proceed through the formation of a heterocyclic iminium species followed by the addition of the organoboron derivative. The diastereoselectivity of this process is discussed. Best results were observed when the probable intermediate was generated from a preformed 3-phenylthiomorpholin-2-ol. Products of this three-component boro-Mannich could be readily converted to the corresponding aminodiols by reduction with lithium aluminium hydride. (c) 2006 Elsevier Ltd. All rights reserved.
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