603985-50-8Relevant academic research and scientific papers
Regio- and enantioselective synthesis of allylic fluorides by electrophilic fluorodesilylation of allyl silanes
Greedy, Benjamin,Paris, Jean-Marc,Vidal, Thierry,Gouverneur, Veronique
, p. 3291 - 3294 (2003)
Enantiopure N-fluorocinchona alkaloids promoted the electrophilic fluorodesilylation of allyl silanes in a conceptually new approach to the regio- and enantioselective formation of allylic fluorides (see scheme). Excellent conversions were observed in these reactions, which afforded the desired allylic fluorides with up to 96% ee.
CHIRAL FLUORINATING REAGENTS
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Page/Page column 50-51, (2014/05/24)
This invention relates to fluorinating agents and, more particularly, to chiral non-racemic fluorinating agents useful for enantioselective fluorination, as well as to their synthesis and use and other subject matter. The fluorinating agents are based on a substituted 1,4-diazabicyclo[2.2.2]octane (DABCO) skeleton and provide electrophillic fluorine enantioselectively.
Cinchona alkaloid catalyzed enantioselective fluorination of allyl silanes, silyl enol ethers, and oxindoles
Ishimaru, Takehisa,Shibata, Norio,Horikawa, Takao,Yasuda, Naomi,Nakamura, Shuichi,Toru, Takeshi,Shiro, Motoo
supporting information; experimental part, p. 4157 - 4161 (2009/03/11)
(Chemical Equation Presented) Catalytic variant: Allyl silanes and silyl enol ethers 1 are good substrates for the catalytic highly enantioselective fluorodesilylation using a combination of a biscinchona alkaloid, N-fluorobenzenesulfonimide (NFSI), and base (see scheme). Pharmaceutically attractive 3-aryl-3-fluorooxindoles such as 3 can also be synthesized with high enantioselectivity.
New approaches to enantioselective fluorination: Cinchona alkaloids combinations and chiral ligands/metal complexes
Shibata, Norio,Ishimaru, Takehisa,Nakamura, Shuichi,Toru, Takeshi
, p. 469 - 483 (2008/01/03)
The selective construction of carbon-fluorine bonds is of great interest to medicinal chemists because the replacement of a hydrogen or an oxygen atom with a fluorine atom in biologically active molecules can confer the molecules with improved physicochem
