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...
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| Published in | Organic letters Vol. 6; no. 12; pp. 1959 - 1962 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
American Chemical Society
10.06.2004
Amer Chemical Soc |
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| Abstract | 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. |
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| AbstractList | Full conversion and en antioselectivities 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. 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. [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. |
| Author | Keeris, Roy Jastrzebski, Johann T. B. H Alexakis, Alexandre Arink, Anne M van Koten, Gerard Benhaim, Cyril Braam, Thijs W Rosset, Stéphane |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/15176793$$D View this record in MEDLINE/PubMed |
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| Keywords | SUBSTITUTION LIGANDS DIETHYLZINC COMPLEXES ORGANOCOPPER 1,4-ADDITION GRIGNARD-REAGENTS |
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| Snippet | Full conversion and enantioselectivities up to 83% have been obtained in the conjugate addition reactions of diethyl zinc to Michael acceptors catalyzed by... Full conversion and en antioselectivities up to 83% have been obtained in the conjugate addition reactions of diethyl zinc to Michael acceptors catalyzed by... [structure: see text] Full conversion and enantioselectivities up to 83% have been obtained in the conjugate addition reactions of diethyl zinc to Michael... |
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| SubjectTerms | 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 |
| Title | Copper(I) Thiolate Catalysts in Asymmetric Conjugate Addition Reactions |
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