Copper(I) thiolate catalysts in asymmetric conjugate addition reactions.
[structure: see text] 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 R(2)Zn reagents afford better results, whereas earlier work showed that RMgX reagents react more selectively with acyclic enones.
Arink
Anne M
AM
Debye Institute, Department of Metal-Mediated Synthesis, Utrecht University, Padualaan 8, 3584 CH Utrecht, The Netherlands.
Braam
Thijs W
TW
Keeris
Roy
R
Jastrzebski
Johann T B H
JT
Benhaim
Cyril
C
Rosset
Stéphane
S
Alexakis
Alexandre
A
van Koten
Gerard
G
D000438:Alcohols / Q000138:chemical synthesis; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D017967:Zinc Compounds / Q000138:chemical synthesis*
D000438:Alcohols; D007659:Ketones; D009942:Organometallic Compounds; D017967:Zinc Compounds; C048402:copper(I)-thiolate