Synthesis of chiral ligands containing the N-( S)-α-phenylethyl group and their evaluation as activators in the enantioselective addition of Et 2Zn to benzaldehyde

Virginia M Mastranzo,Ericka Santacruz,Gabriela Huelgas,Evelyn Paz,Martha V Sosa-Rivadeneyra,Sylvain Bernès,Eusebio Juaristi,Leticia Quintero,Cecilia Anaya De Parrodi

doi:10.1016/j.tetasy.2006.06.005

Synthesis of chiral ligands containing the N-( S)-α-phenylethyl group and their evaluation as activators in the enantioselective addition of Et 2Zn to benzaldehyde

Virginia M Mastranzo, Ericka Santacruz + Show 7 more

https://doi.org/10.1016/j.tetasy.2006.06.005

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Journal: Tetrahedron: Asymmetry	Publication Date: Jul 1, 2006
Citations: 15

Affiliation: Instituto Politécnico Nacional, Center for Research and Advanced Studies of the National Polytechnic Institute, Benemérita Universidad Autónoma de Puebla, Universidad de las Américas Puebla

#Synthesis Of Chiral Ligands #Addition Of Et 2Zn + Show 8 more

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Abstract

The synthesis of chiral ligands 4– 18 derived from N-[( S)-α-phenylethyl]- trans-β-aminocyclohexanols ( S, S, S)- 1a and ( R, R, S)- 2 is described. Addition of diethylzinc to benzaldehyde catalyzed by ligands 4– 18 (6 mol %) proceeds in fair to good yield (45–86%), and low to good enantioselectivities (1–76% ee). Highest enantioselectivities were induced by ligands ( S, S, S)- 4 and ( S, S, S, S, R, R)- 18 (76% and 68% ee, respectively). The configuration of the major enantiomer of carbinol 3 is ( R) in both cases.

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