Enantioselective addition of diethylzinc to aldehydes catalyzed by N-(9-phenylfluoren-9-yl) beta-amino alcohols

MR Paleo; I Cabeza I; FJ Sardina

doi:10.1021/jo9917083

Enantioselective addition of diethylzinc to aldehydes catalyzed by N-(9-phenylfluoren-9-yl) beta-amino alcohols

J Org Chem. 2000 Apr 7;65(7):2108-13. doi: 10.1021/jo9917083.

Authors

MR Paleo¹, I Cabeza I, FJ Sardina

Affiliation

¹ Departamento de Quimica Organica, Facultad de Quimica, Universidad de Santiago de Compostela, Spain.

PMID: 10774033
DOI: 10.1021/jo9917083

Abstract

A set of secondary N-phenylfluorenyl beta-amino alcohols have been prepared and evaluated as catalysts for the enantioselective addition of diethylzinc to benzaldehyde. The influence of the substituents on the stereogenic centers of the ligand has been studied, and enantioselectivities up to 97% have been obtained. Those ligands with bulky groups in the carbinol stereocenter and small groups alpha to the nitrogen atom displayed the best catalytic activity and enantioselectivity. The most enantioselective ligand (4e) was found to possess general applicability for the enantioselective addition of diethylzinc to a variety of aromatic and aliphatic aldehydes.