Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 41, Pages 10888-10900Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200901614
Keywords
aldehydes; cyclization; enynes; gold; homogeneous catalysis; ketones
Categories
Funding
- Deutsche Forschungsgemeinschaft [SFB 623]
- Studienstiftung des deutschen Volkes
- Fonds der Chemischen Industrie
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A full account of a recently discovered gold(I)-catalyzed reaction, a cycloaddition of carbonyl compounds to enynes yielding 2-oxabicyclo[3.1.0]hexanes with four stereogenic centers, is presented. The reaction proceeds with very high diastereoselectivity. The scope of the reaction has been investigated. In addition, experiments and DFT calculations concerning mechanistic aspects were carried out. The reaction course varies with the substitution pattern of the alkene moiety of the starting enyne. Branched olefins led to 2-oxabicyclo[3.1.0]hexanes, terminally substituted olefins proceeded with the incorporation of two carbonyl components to give hexahydrocyclopenta[d][1,3]dioxines.
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