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Synfacts 2009(1): 0046-0046  
DOI: 10.1055/s-0028-1087408
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Hydroarylation-Cycloisomerization of 1,6-Enynes

Contributor(s): Mark Lautens, Frédéric Ménard
P. Y. Toullec, C.-M. Chao, Q. Chen, S. Gladiali, J.-P. Genêt, V. Michelet*
École Nationale Supérieure de Chimie de Paris, France; Università di Sassari, Italy
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Publikationsdatum:
18. Dezember 2008 (online)

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Significance

This catalytic reaction is a good ­example of the atom-economy principle: two C-C bonds are created with good enantio- and excellent diastereoselectivity. Several protocols have been reported for the cycloisomerization of enynes, most employing Au(I) or Pt(II) catalysts, but highly enantioselective processes have remained elusive. The authors opted to tackle this challenge with a Pt(II) catalyst for its ability to accept four ligands, whereas Au(I) is limited to two.