104461-84-9Relevant academic research and scientific papers
An expedient synthesis of cyanoformates via DAST-mediated C–C bond cleavage of α-oximino-β-ketoesters
Kim, Danhee,Lim, Hee Nam
supporting information, (2021/05/10)
A new protocol to synthesize cyanoformates was developed using simple β-ketoesters as substrates. (Diethylamino)sulfur trifluoride (DAST) was used as a dual-role reagent to activate the oxime moiety and to donate a fluoride. The key intermediates, α-oximino-β-ketoesters, were prepared by highly efficient acid-assisted oximation of β-ketoesters. Then, the deconstruction of α-oximino-β-ketoesters by the fluorinative C–C bond cleavage was demonstrated to provide cyanoformates. In this event, the fluoride addition followed by the C–C bond cleavage selectively occurred in the ketones over esters. Due to simple and mild reaction conditions, variously functionalized cyanoformates were exemplified.
Enantioselective and diastereoselective syntheses of cyanohydrin carbonates
Belokon', Yuri N.,Clegg, William,Harrington, Ross W.,Ishibashi, Eisuke,Nomura, Hiroshi,North, Michael
, p. 9724 - 9740 (2008/02/12)
A new and general synthesis of alkyl cyanoformates is presented starting from the appropriate alcohol and oxalyl chloride. This is used to prepare enantiomerically pure cyanoformates from enantiomerically pure primary and secondary alcohols. Optimal condi
BOTRYDIAL SYNTHETIC STUDIES. ASYMMETRIC SYNTHESIS OF QUATERNARY CARBON CENTRES.
Kunisch, Franz,Hobert, Kurt,Welzel, Peter
, p. 5433 - 5436 (2007/10/02)
The synthesis of the optically active 4 has been accomplished by asymmetric formation of cyclic β-keto esters fully substituted at the α Carbon followed by chemoselective reduction of the ester group.Of the asymmetric reactions examined the Koga procedure proved to be the most selective.
