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Synfacts 2010(1): 0077-0077
DOI: 10.1055/s-0029-1218469
DOI: 10.1055/s-0029-1218469
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper-Catalyzed Asymmetric Allylic Arylation with Grignard Reagents
K. B. Selim, Y. Matsumoto, K.-i. Yamada, K. Tomioka*
Kyoto University, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. Dezember 2009 (online)
Significance
The copper-catalyzed asymmetric allylic alkylation is a well-established and valuable transformation. The analogous reaction utilizing aryl nucleophiles is much less developed. The asymmetric allylic arylation reaction often suffers from low enantioselectivity and poor linear/branched ratios (Chem. Commun. 2008, 5140). The authors report a significant advancement in this field by the addition of aryl Grignard reagents to cinnamyl-like allylic halides. The chiral branched products resulting from γ-addition are formed with good yields, regioselectivity, and enantioselectivity.