24730-98-1Relevant academic research and scientific papers
Tuning the Reactivity of Functionalized Diallylic Alcohols: Br?nsted versus Lewis Acid Catalysis
Lempenauer, Luisa,Du?ach, Elisabet,Lemière, Gilles
supporting information, p. 10285 - 10288 (2017/08/07)
The chemodivergent reactivity of bifunctional, enol thioether-containing diallylic alcohols in acidic medium is disclosed, highlighting the difference between strong Lewis acid and mild Br?nsted acid catalysis. In the presence of bismuth(III) triflate, allylic alcohol activation affords diversely substituted cyclopentenones in a Nazarov-type electrocyclization, whereas activation of the thioenol ether by p-toluenesulfonic acid provides an entry to α-sulfenylated β,γ-unsaturated ketones. Both methods represent a facile access to the corresponding products under mild conditions, using inexpensive and non-toxic catalytic systems.
Access to functionalized bicyclo[4,3,0]nonenes via palladium-catalyzed oxidative cyclization of 2-allylcyclohexyl oximes
Zhu, Jia-Liang,Wu, Sih-Ting,Shie, Jr-Yun
, p. 3623 - 3633 (2014/05/06)
A new palladium-catalyzed oxidative cyclization process leading to the functionalized bicyclo[4,3,0]nonenes is serendipitously discovered during attempts to form aza-heterocycle by the amino-Heck reaction of trans-2-vinylclohexyl phosphinyloxime. Under the influence of Pd(dba) 2/Et3N/1:1 N2-O2 (1:1, v/v) (Method A) or Pd(OAc)2/Et3N/O2 (Method B), the reactions afford the substituted cis-1-hydroxyl-8-formyl-bicyclo[4,3,0]non-8(9)- enes or bicycle[4,3,0]non-1(9)-en-8-ones in varying yields with the incorporation of molecular oxygen into the structures. The 5,6-bicyclic scaffold of these products is presumably derived from tandem double intramolecular cyclization followed by the ring-opening of an aza-palladium(II) tricyclic intermediate.
