Concepedia

Effect of Ligand Structure on the Zinc-Catalyzed Henry Reaction. Asymmetric Syntheses of (−)-Denopamine and (−)-Arbutamine

Barry M. Trost, Vince S. C. Yeh, Hisanako Ito, Nadine Bremeyer

Organic Letters · 2002 · 265 citations · 19 references

DOI

Concepts

Abstract

[reaction: see text] Syntheses of variously modified ligands for the dinuclear zinc catalysts for the asymmetric aldol and nitroaldol (Henry) reactions are reported. Catalytic enantioselective nitroaldol reactions promoted by these modified ligands led to efficient syntheses of the beta-receptor agonists (-)-denopamine and (-)-arbutamine.

References

19

Asymmetric Catalysis with Heterobimetallic Compounds

Masakatsu Shibasaki, Hiroaki Sasai, Takayoshi Arai · Angewandte Chemie International Edition in English · 1997 · 691 citations

, , +16

Basic character of rare earth metal alkoxides. Utilization in catalytic carbon-carbon bond-forming reactions and catalytic asymmetric nitroaldol reactions

Hiroaki Sasai, Takeyuki Suzuki, Shigeru Arai et al. · Journal of the American Chemical Society · 1992 · 604 citations

, , +7

A Direct Catalytic Enantioselective Aldol Reaction via a Novel Catalyst Design

Barry M. Trost, Hisanaka Ito · Journal of the American Chemical Society · 2000 · 501 citations

, , +13

A Dinuclear Zn Catalyst for the Asymmetric Nitroaldol (Henry) Reaction We thank the National Science Foundation and the National Institutes of Health, General Medical Sciences, for their generous support of our programs. Mass spectra were provided by the Mass Spectrometry Facility of the University of California, San Francisco, supported by the NIH Division of Research Resources.

Barry M. Trost, Vince S. C. Yeh · Angewandte Chemie International Edition · 2002 · 338 citations

, , +10

Asymmetric Aldol Reaction via a Dinuclear Zinc Catalyst:  α-Hydroxyketones as Donors

Barry M. Trost, Hisanaka Ito, Elliad R. Silcoff · Journal of the American Chemical Society · 2001 · 309 citations

, , +12