Prev. Article Next Article Table of Contents

Letter

Enantioselective Cu-Catalyzed Conjugate Addition of Diethylzinc to Acyclic Aliphatic Enones

Supporting Info

Andrew P. Duncan and James L. Leighton*

Department of Chemistry, Columbia University, New York, New York 10027

Org. Lett., 2004, 6 (22), pp 4117–4119

DOI: 10.1021/ol048191o

Publication Date (Web): October 8, 2004

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, leighton@chem.columbia.edu

Abstract

A new P-chiral phosphine bis(sulfonamide) ligand has been developed that allows the Cu-catalyzed enantioselective conjugate addition of Et₂Zn to acyclic aliphatic enones. The reactions proceed with excellent levels of enantioselectivity (90−95% ee) with a range of enone substrates, involve the use of only 1.2 equiv of Et₂Zn, and give best results at ambient temperature.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue October 28, 2004
Received September 7, 2004

Recommend & Share

Related Content

Highly Practical and Enantioselective Cu-Catalyzed Conjugate Addition of Alkylzinc Reagents to Cyclic Enones at Ambient TemperatureOrganic Letters
- Highly Practical and Enantioselective Cu-Catalyzed Conjugate Addition of Alkylzinc Reagents to Cyclic Enones at Ambient Temperature
  Isaac J. Krauss and James L. Leighton
  Organic Letters 2003 5 (18), pp 3201–3203
  Abstract: A new ligand for Cu-catalyzed enantioselective additions of dialkylzincs to cyclic enones has been developed. In addition to providing good to excellent enantioselectivities with a range of cyclic enones and dialkylzincs, the ligand has several notworthy ...
  Abstract | Full Text HTML | Hi-Res PDF
Efficient Asymmetric Synthesis of (+)-SCH 351448Organic Letters
- Efficient Asymmetric Synthesis of (+)-SCH 351448
  Sergei Bolshakov and James L. Leighton
  Organic Letters 2005 7 (17), pp 3809–3812
  Abstract: An efficient and stereocontrolled total synthesis of (+)-SCH 351448, a novel activator of low-density lipoprotein receptor promoter, has been achieved with a longest linear sequence of 21 steps. Key steps include applications of the recently developed ...
  Abstract | Full Text HTML | Hi-Res PDF
Cu-Catalyzed Asymmetric Conjugate Additions of Alkylzinc Reagents to Acyclic Aliphatic EnonesJournal of the American Chemical Society
- Cu-Catalyzed Asymmetric Conjugate Additions of Alkylzinc Reagents to Acyclic Aliphatic Enones
  Hirotake Mizutani, Sylvia J. Degrado, and Amir H. Hoveyda
  Journal of the American Chemical Society 2002 124 (5), pp 779–781
  Abstract: Cu-catalyzed enantioselective conjugate additions to acyclic aliphatic enones are reported. The resulting enolates may be functionalized intra- and intermolecularly, leading to the formation of an additional C−C bond. The utility of the present method is ...
  Abstract | Full Text HTML | Hi-Res PDF

Letter

Enantioselective Cu-Catalyzed Conjugate Addition of Diethylzinc to Acyclic Aliphatic Enones

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Highly Practical and Enantioselective Cu-Catalyzed Conjugate Addition of Alkylzinc Reagents to Cyclic Enones at Ambient Temperature

Efficient Asymmetric Synthesis of (+)-SCH 351448

Cu-Catalyzed Asymmetric Conjugate Additions of Alkylzinc Reagents to Acyclic Aliphatic Enones

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES