1402352-83-3Relevant academic research and scientific papers
Catalytic Asymmetric Synthesis of α,α-Difluoromethylated and α-Fluoromethylated Tertiary Alcohols
Huang, Wei-Sheng,Delcourt, Marie-Leónie,Pannecoucke, Xavier,Charette, André B.,Poisson, Thomas,Jubault, Philippe
, p. 7509 - 7513 (2019)
The catalytic asymmetric synthesis of α,α-difluoromethylated tertiary alcohols is described, using an asymmetric dihydroxylation reaction. This protocol using either the AD-mix-α or AD-mix-β allowed an easy access to these valuable fluorinated chiral buil
Asymmetric Organocatalytic Synthesis of Fluorinated β-Hydroxy Diazenes
Matador, Esteban,de Gracia Retamosa, María,Jiménez-Sánchez, Antonio,Monge, David,Fernández, Rosario,Lassaletta, José M.
supporting information, p. 130 - 138 (2018/12/13)
The nucleophilic addition of formaldehyde tert-butyl hydrazone to fluoromethyl ketones provides a valuable tool for the synthesis of highly functionalized β-hydroxy β-tri- and difluoromethyl diazenes. Excellent reactivities and moderate to good enantioselectivities (up to 90 % ee) were achieved by H-bonding activation exerted by tert-Leucine derived H-bonding (squaramide or thiourea) organocatalysts. Subsequent derivatizations in one-pot fashion provide synthetically useful intermediates for target-oriented synthesis: tri- and di-fluoromethylated azoxy compounds, β-amino alcohols, α-hydroxy aldoximes and derivatives thereof.
Highly enantioselective addition of dimethylzinc to fluorinated alkyl ketones, and the mechanism behind it
Neves-Garcia, Tomaz,Vélez, Andrea,Martínez-Ilarduya, Jesús M.,Espinet, Pablo
supporting information, p. 11809 - 11812 (2018/11/21)
Chiral-diamine catalyzed addition of ZnMe2 to PhC(O)CF2X (in dichloromethane at -30 °C) affords fluorinated alkyl tertiary alcohols in high yield (quantitative for X = H, F, Cl; 84% for X = CF3) and up to 99% ee. These con
Tuning the reactivity of difluoromethyl sulfoximines from electrophilic to nucleophilic: Stereoselective nucleophilic difluoromethylation of aryl ketones
Shen, Xiao,Zhang, Wei,Ni, Chuanfa,Hu, Jinbo,Gu, Yucheng
supporting information, p. 16999 - 17002,4 (2020/09/02)
A stereoselective synthesis of enantiomerically enriched difluoromethyl tertiary alcohols by tuning the reactivity of difluoromethyl sulfoximines from electrophilic to nucleophilic difluoromethylating agents is reported. The key feature of this chemistry is the diastereoselective addition of the difluoromethyl sulfoximine to the prochiral carbon of the ketone. The present method was used to prepare enantiomerically enriched difluoromethyl secondary alcohols and difluorinated analogues of the natural products gossonorol and boivinian B, demonstrating the potency of the method.
