96746-40-6Relevant academic research and scientific papers
How an early or late transition state impacts the stereoselectivity of tetrahydropyran formation by intramolecular oxa-Michael addition
Bates, Roderick W.,Csókás, Dániel,Ho, Annabel Xuan Ying,Ramabhadran, Raghunath O.
, p. 6293 - 6304 (2019)
The intramolecular oxa-Michael addition giving tetrahydropyrans has been examined experimentally using both acidic and basic catalysis. With acidic catalysis, the diequatorial product is exclusively obtained in a kinetically controlled reaction in all cas
Remote C(sp3)?H Arylation and Vinylation of N-Alkoxypyridinium Salts to δ-Aryl and δ-Vinyl Alcohols
Bao, Xu,Wang, Qian,Zhu, Jieping
supporting information, (2019/08/21)
The reaction of readily available and bench-stable N-alkoxypyridinium salts with arylboronic and vinylboronic acids afforded δ-aryl and δ-vinyl alcohols, respectively, in the presence of fac-Ir(ppy)3 and Cu(OTf)2 dual catalysts. The reaction takes place through a domino process involving the reductive generation of alkoxyl radicals, 1,5-hydrogen atom transfer (1,5-HAT) and the copper-catalyzed cross-coupling reaction of the resulting translocated carbon radicals with boronic acids. Complementary to the Minisci reaction, this method allows for the arylation of nucleophilic alkyl radicals with both electron-rich and electron-poor arenes under mild reaction conditions.
Stereoselective Cyclization of 4-Substituted 5-Hexen-1-ols and Related Compounds by Benzeneselenenyl Triflate
Inoue, Hirohumi,Murata, Shizuaki,Suzuki, Toshiyasu
, p. 901 - 910 (2007/10/02)
Oxyselenylation of 4-substituted 5-hexen-1-ols 1 with benzeneselenenyl trifluoromethanesulfonate proceeds by intramolecular exo cyclization stereoselectively to give 3-substituted trans- or cis-2-(phenylselenenylmethyl)tetrahydropyrans 3.Formation of the trans isomers is favored when the substituents contain alkyl or phenyl substituents in the 4-position, whereas the cis isomers predominate when the substituents are alkoxyalkyl, alkoxyl, acyl, and hydroxyl.The mechanism of the trans and cis stereoselectivity is explained by steric and electronic effects in the phenylseleniranium intermediates, 7 and 8. - Key Words: Oxyselenenylation / Benzeneselenenyl triflate / Selenium compounds / Trifluoromethanesulfonate / Alkenols
