339312-91-3Relevant academic research and scientific papers
The first examples of successful anionic oxy-ene reactions
Schmid, Gavin A.,Borschberg, Hans-Juerg
, p. 401 - 415 (2007/10/03)
The first examples of successful anionic oxy-ene reactions are reported. The corresponding reactions 16 - 15 (Li+ as counter ion) and 18 - 21 (K- as counter ion) proceeded with good yields and high diastereoselectivities. In the latter case, the reaction proceeds under very mild conditions (3 h reflux in toluene) in 65% yield with more than 96% d/s. However, when the phosphazene base P4-(t-Bu) was allowed to interact with the same or similar substrates, entirely different products resulted at ambient temperature. In the case of 1, the benzoyl-dibenzocyclooctene 4 was formed in 80% yield, while treatment of the closely related substrate 8 furnished the cyclobutanol derivative 11 with similar efficiency. In both case, the unexpected product structures were established by means of X-ray crystallography.
