Tetrahedron: Asymmetry

Synthesis of chiral C/N-functionalized morpholine alcohols: study of their catalytic ability as ligand in asymmetric diethylzinc addition to aldehyde

R Dave, NA Sasaki

Index: Dave, Rajesh; Sasaki, N. Andre Tetrahedron Asymmetry, 2006 , vol. 17, # 3 p. 388 - 401

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Citation Number: 41

Abstract

A broad variety of chiral C/N-functionalized morpholine alcohols sharing a common structural motif in the 3-(hydroxymethyl) morpholine 6 were prepared from enantiomerically pure serine for the purpose of studying their catalytic ligand properties. The asymmetric addition of diethylzinc to benzaldehyde in the presence of 10mol% of chiral C/N- functionalized morpholine alcohols gave 1-phenyl-1-propanol in 59–81% yield with 10– ...