Tetrahedron: Asymmetry

Novel C 2-symmetric chiral O, N, N, O-tetradentate 2, 2-bipyridyldiolpropane ligands: synthesis and application in asymmetric diethylzinc addition to aldehydes

YS Shih, R Boobalan, C Chen, GH Lee

Index: Shih, Yi-Shan; Boobalan, Ramalingam; Chen, Chinpiao; Lee, Gene-Hsian Tetrahedron Asymmetry, 2014 , vol. 25, # 4 p. 327 - 333

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Citation Number: 3

Abstract

Abstract First synthesis of C 2-symmetric chiral O, N, N, O-tetradentate 2, 2- bipyridyldiolpropane ligands is described. The Mukaiyama–Michael reaction was applied as an important reaction for the synthesis of 2, 2-bipyridylpropane 9. Among the ligands synthesized, ligand 11 exhibits excellent chiral induction (up to 97% ee) in diethylzinc addition to various aldehydes. The use of additional Lewis acid such as Ti (O i Pr) 4 in ...