4.5 Article

Enamine-Metal Lewis Acid Bifunctional Catalysis: Application to Direct Asymmetric Aldol Reaction of Ketones

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 27, Pages 4581-4585

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900678

Keywords

Organocatalysis; Aldol reactions; Lewis acids; Lewis bases; Amino acids; Tridendate ligands

Funding

  1. Miami University

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Unprecedented bifunctional enamine-metal Lewis acid catalysts have been developed. In this bifunctional catalytic system, a tridentate ligand tethered with a chiral secondary amine was designed to solve the acid-base self-quenching problem leading to catalyst inactivation. This new bifunctional enamine-metal Lewis acid catalyst was found to catalyze aldol reactions of ketones efficiently in high yields and good to excellent diastereoselectivities and enantioselectivities. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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