Synthesis of seven-membered carbocyclic rings via a microwave-assisted tandem oxyanionic 5-exo dig cyclization-claisen rearrangement process.
Appropriately substituted 1-alkenyl-4-pentyn-1-ol systems, readily prepared from simple starting materials, serve as useful precursors to a number of substituted cyclohept-4-enone derivatives via a microwave-assisted tandem oxyanionic 5-exo cyclization/Claisen rearrangement sequence. The reactions involving terminally substituted 4-pentyn-1-ols were found to be highly stereoselective, with the alpha and beta groups in the final product showing a strong preference for the trans orientation.
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Xin
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Department of Chemistry, Connecticut College, 270 Mohegan Avenue, New London, Connecticut 06320, USA.
Kyne
Robert E
RE
Ovaska
Timo V
TV
D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D008872:Microwaves; D021241:Spectrometry, Mass, Electrospray Ionization