jo0710432_si_004.pdf (52.7 kB)
Synthesis of Seven-Membered Carbocyclic Rings via a Microwave-Assisted Tandem Oxyanionic 5-exo dig Cyclization−Claisen Rearrangement Process
journal contribution
posted on 2007-08-17, 00:00 authored by Xin Li, Robert E. Kyne, Timo V. OvaskaAppropriately 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 α and
β groups in the final product showing a strong preference
for the trans orientation.