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Synfacts 2011(6): 0639-0639  
DOI: 10.1055/s-0030-1260438
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of γ-Butenolides via Sequential Metal-Catalyzed Reactions

Contributor(s): Hisashi Yamamoto, Zhi Li
B. Mao, K. Geurts, M. Fañanás-Mastral, A. W. van Zijl, S. P. Fletcher, A. J. Minnaard, B. L. Feringa*
University of Groningen, The Netherlands
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Publication History

Publication Date:
19 May 2011 (online)

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Significance

This paper describes a general two-step asymmetric synthesis of γ-butenolides bearing a γ-chiral center. The first step is the copper-catalyzed hetero-allylic asymmetric alkylation developed in the same group (J. Am. Chem. Soc. 2006, 128, 15572) followed by ring-closing meta­thesis. A similar strategy has also been applied in an allylic asymmetric alkylation-ring-closing meta­thesis sequence (F. Giacomina, D. Riat, A. Alexakis Org. Lett. 2010, 12, 4658).