Prev. Article Next Article Table of Contents

Communication

A New Copper Acetate-Bis(oxazoline)-Catalyzed, Enantioselective Henry Reaction

Supporting Info

David A. Evans,* Daniel Seidel, Magnus Rueping, Hon Wai Lam, Jared T. Shaw, and C. Wade Downey

Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138

J. Am. Chem. Soc., 2003, 125 (42), pp 12692–12693

DOI: 10.1021/ja0373871

Publication Date (Web): September 27, 2003

Abstract

A highly enantioselective, nitroaldol reaction catalyzed by a chiral Cu(II) bis(oxazoline) complex has been developed. The reaction scope includes both aromatic and aliphatic aldehydes (15 examples) affording products in good yields and enantioselectivities (87−94% ee). An X-ray structure of the catalyst has been provided along with a rationalization of the sense of asymmetric induction.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

Explore by:

Author of this Article Any Author Research Topic

History

Published In Issue October 22, 2003
Received July 18, 2003

Recommend & Share

Related Content

Practical Asymmetric Henry Reaction Catalyzed by a Chiral Diamine-Cu(OAc)₂ ComplexOrganic Letters
- Practical Asymmetric Henry Reaction Catalyzed by a Chiral Diamine-Cu(OAc)₂ Complex
  Takayoshi Arai, Masahiko Watanabe, and Akira Yanagisawa
  Organic Letters 2007 9 (18), pp 3595–3597
  Abstract: The chiral diamine ligand 3 was designed and synthesized from (R,R)-1,2-diphenylethylenediamine, (S)-2,2‘-dibromomethyl-1,1‘-binaphthalene, and o-xylylene dibromide. The resulting 3-Cu(OAc)₂ complex was a highly efficient catalyst for the Henry reaction, ...
  Abstract | Full Text HTML | Hi-Res PDF
Enantioselective Nitroaldol Reaction of α-Ketoesters Catalyzed by Cinchona AlkaloidsJournal of the American Chemical Society
- Enantioselective Nitroaldol Reaction of α-Ketoesters Catalyzed by Cinchona Alkaloids
  Hongming Li, Baomin Wang, and Li Deng
  Journal of the American Chemical Society 2006 128 (3), pp 732–733
  Abstract: The development of highly enantioselective and general catalytic nitroaldol (Henry) reactions with ketones is a challenging yet desirable task in organic synthesis. In this communication, we report an asymmetric nitroaldol reaction with α-ketoesters ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Effect of Ligand Structure on the Zinc-Catalyzed Henry Reaction. Asymmetric Syntheses of (−)-Denopamine and (−)-ArbutamineOrganic Letters
- 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, and Nadine Bremeyer
  Organic Letters 2002 4 (16), pp 2621–2623
  Abstract: 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 ...
  Abstract | Full Text HTML | Hi-Res PDF

Communication

A New Copper Acetate-Bis(oxazoline)-Catalyzed, Enantioselective Henry Reaction