Journal
TETRAHEDRON LETTERS
Volume 45, Issue 18, Pages 3569-3572Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2004.03.063
Keywords
solid phase organic synthesis; alpha-hydrazinoacid; mitsunobu reaction; protecting group
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The first solid phase synthesis of chiral alpha-hydrazinoacids has been developed. This synthesis was achieved by the preparation of solid supported-N-alkyloxycarbonyl-aminophthalimides used as acidic partners in the Mitsunobu protocol involving alpha-hydroxyesters. Two different final trans-protection steps of the phthaloyl group, developed first in liquid phase, result in efficient releases of orthogonally bis-protected or fully tris-protected hydrazine derivatives. A comparison between liquid and solid phase syntheses is outlined: even if the overall yields are sometimes rather higher by the liquid phase synthesis, the on-resin protocol is much more rapid and convenient than the liquid protocol. (C) 2004 Elsevier Ltd. All rights reserved.
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