791809-52-4Relevant academic research and scientific papers
Asymmetric Catalytic Epoxidation of Terminal Enones for the Synthesis of Triazole Antifungal Agents
Feng, Xiaoming,He, Qianwen,Liu, Xiaohua,Zhang, Dong,Zhang, Fengcai
supporting information, p. 6961 - 6966 (2021/09/11)
An enantioselective epoxidation of α-substituted vinyl ketones was realized to construct the key epoxide intermediates for the synthesis of various triazole antifungal agents. The reaction proceeded efficiently in high yields with good enantioselectivities by employing a chiral N,N′-dioxide/ScIII complex as the chiral catalyst and 35% aq. H2O2 as the oxidant. It enabled the facile transformation for optically active isavuconazole, efinaconazole, and other potential antifungal agents.
Preparation and regioselective SN2′ reaction of novel gem-difluorinated vinyloxiranes with RLi
Ueki, Hisanori,Chiba, Takashi,Yamazaki, Takashi,Kitazume, Tomoya
, p. 7616 - 7627 (2007/10/03)
A series of hitherto unknown 3,4-epoxy-1,1-difluorobutenes were prepared from the readily accessible α,β-epoxy ketones and these compounds were found to undergo regioselective SN2′ reactions with hard RLi nucleophiles occurring at the highly positively charged terminal fluorine-possessing sp2 carbon atom in quite sharp contrast to the cases of the corresponding nonfluorinated vinyloxiranes which only attained a low level of regioselectivity. Addition of HMPA substantially improved the products' olefinic stereoselectivity. Theoretical calculations were used to qualitatively explore the nature of selectivity in these reactions.
