Tetrahedron: Asymmetry

Catalysed asymmetric reaction of aldehydes with dialkylzinc in the presence of chiral pyridyl alcohols as ligands

M Ishizaki, K Fujita, M Shimamoto, O Hoshino

Index: Ishizaki; Fujita; Shimamoto; Hoshino Tetrahedron Asymmetry, 1994 , vol. 5, # 3 p. 411 - 424

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Citation Number: 79

Abstract

Abstract The synthesis of homochiral pyridyl alcohols (1, 2, 3a-c) and a catalytic asymmetric addition of dialkylzinc to various aldehydes using 1-3 as ligands are described. Although the reaction of benzaldehyde with Et 2 Zn in the presence of (S)-1 and (R, R)-2 gave (S)-and (R)- 1-phenyl-1-propanol, respectively, in moderate enantiomeric excess (ee), tridentate ligands (3a-c) accelerated the reaction to produce the corresponding alcohols in high ee ...