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Synfacts 2008(5): 0494-0494  
DOI: 10.1055/s-2008-1072648
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium(I)-Catalyzed Cycloaddition of 1,6-Enynes and Electron-Deficient Ketones

Contributor(s): Hisashi Yamamoto, Marina Naodovic
K. Tanaka*, Y. Otake, H. Sagae, K. Noguchi, M. Hirano
Tokyo University of Agriculture and Technology, Japan
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Publication History

Publication Date:
23 April 2008 (online)

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Significance

Rh(I)-catalyzed [2+2+2] cycloaddition of 1,6-enynes with electron-deficient ketones successfully produces fused dihydropyrans in highly regio-, diastereo-, and enantioselective manner. Main advantage of this methodology is easy access to complex heterocyclic structures that possess two quaternary stereocenters (product 1). It is also shown that electron-rich ketones can be utilized to yield ortho-substituted aryl ketones (product 2).