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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Veröffentlicht in:	Organic letters 2004-06, Vol.6 (12), p.1959-1962
Hauptverfasser:	Arink, Anne M, Braam, Thijs W, Keeris, Roy, Jastrzebski, Johann T. B. H, Benhaim, Cyril, Rosset, Stéphane, Alexakis, Alexandre, van Koten, Gerard
Format:	Artikel
Sprache:	eng
Schlagworte:	Alcohols - chemical synthesis Catalysis Ketones - chemical synthesis Molecular Structure Organometallic Compounds - chemical synthesis Organometallic Compounds - chemistry Stereoisomerism Zinc Compounds - chemical synthesis
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Beschreibung
Zusammenfassung:	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.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol049457u