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Synfacts 2011(11): 1203-1203  
DOI: 10.1055/s-0031-1289210
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Alder-Ene Reactions towards Dihydrobenzofurans

Contributor(s): Mark Lautens, Stephen G. Newman
R. Okamoto, E. Okazaki, K. Nogushi, K. Tanaka*
Tokyo University of Agriculture and Technology, Koganei, Japan
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Publikationsverlauf

Publikationsdatum:
19. Oktober 2011 (online)

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Significance

Many complex ring systems can be accessed by enantioselective cycloisomerization reactions. The transition-metal-catalyzed 1,6-enyne isomerization is a particular well-developed cycloisomerization (see Review below). The authors have combined the asymmetric rhodium-catalyzed Alder-ene reaction with an olefin isomerization process to prepare chiral dihydrobenzofurans in a domino fashion.

Review: V. Michelet, P. Y. Toullec, J.-P. Genêt ­Angew. Chem. Int. Ed. 2008, 47, 4268-4315.