Gold-catalyzed reactivity of 3-silyloxy-1,5-enynes: a synthetic tool for the synthesis of complex structures and its limitations

Gold-catalyzed reactions of 3-silyloxy-1,5-enynes in the presence of sterically demanding alcohols afford 4-acylcyclopentenes. The cascade process most likely proceeds through a 6- endo- dig carbocyclization and subsequent pinacol-type rearrangement. Studies that define scope and limitations of the...

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Bibliographic Details
Published inTetrahedron Vol. 65; no. 9; pp. 1880 - 1888
Main Authors Menz, Helge, Binder, Jörg T., Crone, Benedikt, Duschek, Alexander, Haug, Timm T., Kirsch, Stefan F., Klahn, Philipp, Liébert, Clémence
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.02.2009
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
EFFICIENT ACCESS
CASCADE REACTIONS
DOMINO REACTIONS
GOLD(I)-CATALYZED FORMATION
C-C
STRATEGIC USE
SKELETAL REARRANGEMENT
PRINS CYCLIZATIONS
CYCLOISOMERIZATION REACTIONS
HIGHLY SUBSTITUTED FURANS
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Summary:Gold-catalyzed reactions of 3-silyloxy-1,5-enynes in the presence of sterically demanding alcohols afford 4-acylcyclopentenes. The cascade process most likely proceeds through a 6- endo- dig carbocyclization and subsequent pinacol-type rearrangement. Studies that define scope and limitations of the cyclization–migration strategy are also described. An alternative cascade yields highly substituted aryls through an unprecedented cyclization–fragmentation pathway. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.11.103