Copper(I) Thiolate Catalysts in Asymmetric Conjugate Addition Reactions

Full conversion and enantioselectivities up to 83% have been obtained in the conjugate addition reactions of diethyl zinc to Michael acceptors catalyzed by well-defined (chiral) copper(I) aminoarenethiolates. Interesting differences between organozinc or Grignard reagents have been found:  for cycli...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 6; no. 12; pp. 1959 - 1962
Main Authors Arink, Anne M, Braam, Thijs W, Keeris, Roy, Jastrzebski, Johann T. B. H, Benhaim, Cyril, Rosset, Stéphane, Alexakis, Alexandre, van Koten, Gerard
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.06.2004
Amer Chemical Soc
Subjects
Alcohols - chemical synthesis
Catalysis
Chemistry
Chemistry, Organic
Ketones - chemical synthesis
Molecular Structure
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Zinc Compounds - chemical synthesis
SUBSTITUTION
LIGANDS
DIETHYLZINC
COMPLEXES
ORGANOCOPPER
1,4-ADDITION
GRIGNARD-REAGENTS
Online AccessGet full text

Cover

More Information
Summary:Full conversion and enantioselectivities up to 83% have been obtained in the conjugate addition reactions of diethyl zinc to Michael acceptors catalyzed by well-defined (chiral) copper(I) aminoarenethiolates. Interesting differences between organozinc or Grignard reagents have been found:  for cyclic enones R2Zn reagents afford better results, whereas earlier work showed that RMgX reagents react more selectively with acyclic enones.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol049457u