Journal
TETRAHEDRON-ASYMMETRY
Volume 18, Issue 24, Pages 2923-2946Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2007.11.034
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This paper outlines our efforts to study the influence of an oxygen atom adjacent to the stereogenic center of beta-aminoalcohol derivatives used as ligands for catalysts in the asymmetric alkylation of aldehydes. Thirty-four enantiomerically pure (S)-dihydrofuran-2-yl, (S)-tetrahydrofuran-2-yl-, and furan-2-yl-beta-dialkylamino alcohols have been prepared from 1,4:3,6-dianhydromannitol, 1,4:3,6-dianhydrosorbitol, and aminoacids, and then have been evaluated as ligands for the enantio selective addition of diethylzinc to benzaldellyde. Attention has been focused on the structural features governing the extent of chiral induction, the reaction rate, and the chemical yield of I-phenyl-l-propanol which has been promoted by this wide collection of beta-dialkylamino alcohols. (c) 2007 Elsevier Ltd. All rights reserved.
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