Journal
TETRAHEDRON
Volume 62, Issue 7, Pages 1390-1401Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.11.028
Keywords
aldol-type reaction; alpha-diazo-beta-hydroxyester; alpha-amino-beta-hydroxyester
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The one-pot synthesis of alpha-diazo-beta-hydroxyesters from sodium azide under phase-transfer-catalyzed conditions has been achieved. This protocol includes three different chemical transformations promoted by a single catalyst in each step to give products in good to excellent yields. The reaction was applied to a catalytic asymmetric aldol-type reaction Using alpha-diazoesters with aldehydes in the presence of a chiral quaternary ammonium salt and gave products with up to 81% ee. The diastereoselective transformation of the products to chiral alpha-amino-beta-hydroxyester derivatives is also described. (c) 2005 Elsevier Ltd. All rights reserved.
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