Tetrahedron

Enantioselective synthesis of 1, 2-, 1, 3-and 1, 4-aminoalcohols by the addition of dialkylzincs to 1, 2-, 1, 3-and 1, 4-aminoaldehydes

C Lutz, V Lutz, P Knochel

Index: Lutz, Christian; Lutz, Volker; Knochel, Paul Tetrahedron, 1998 , vol. 54, # 23 p. 6385 - 6402

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Citation Number: 69

Abstract

Chiral 1, 3-and 1, 4-aminoalcohols were prepared by the addition of functionalized dialkylzincs to 1, 3-aliphatic and 1, 4-unsaturated aminoaldehydes with good to excellent enantioselectivity. Syn-or anti-1, 2-aminoalcohols are stereoselectively obtained by asymmetric addition of dialkylzincs to α-aminoaldehydes depending on the choice of the chiral catalyst. A chelate controlled addition is observed if less than stoichiometric ...