132716-06-4Relevant academic research and scientific papers
Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis
Daniliuc, Constantin G.,Gilmour, Ryan,Neufeld, Jessica,Sarie, Jér?me C.,Thiehoff, Christian
, p. 15069 - 15075 (2020)
The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF2 enables the direct fluorocyclization of allyl phenyl ethers to generate novel scaffolds that manifest the stereoelectronic gauche effect. Mechanistic interrogation using deuterated probes confirms a stereospecific process consistent with a type IIinv pathway.
A NEW METHOD FOR THE in Situ GENERATION OF Cp2Zr(H)Cl (SCHWARTZ' REAGENT)
Lipshutz, Bruce H.,Keil, Robert,Ellsworth, Edmund L.
, p. 7257 - 7260 (2007/10/02)
Treatment of Cp2ZrCl2 with LiEt3BH in THF leads to formation of Cp2Zr(H)Cl.Subsequently introduced terminal acetylenes undergo hydrozirconation without compromising acid-sensitive functionality present in the alkyne.
