66221-85-0Relevant academic research and scientific papers
Synthesis of enantiopure 1,4-dioxanes, morpholines, and piperazines from the reaction of chiral 1,2-diols, amino alcohols, and diamines with vinyl selenones
Bagnoli, Luana,Scarponi, Catalina,Rossi, Maria Giovanna,Testaferri, Lorenzo,Tiecco, Marcello
scheme or table, p. 993 - 999 (2011/03/20)
The reactions of readily available vinyl selenones with enantiopure 1,2-diols, N-protected-1,2-aminoalcohols, and diamines gave substituted enantiopure 1,4-dioxanes, morpholines, and piperazines, respectively, in good to excellent yields. The same procedu
Preparation of both enantiomers of cyclopropane derivatives from the reaction of vinyl selenones with di-(-)-bornyl malonate
Bagnoli, Luana,Scarponi, Catalina,Testaferri, Lorenzo,Tiecco, Marcello
experimental part, p. 1506 - 1514 (2009/12/01)
The reaction of vinyl selenones with di-(-)-bornyl malonate and sodium hydride occurred with low diastereoselectivity and afforded a mixture of two diastereomeric cyclopropane derivatives in comparable yields. These, however, could be easily separated by chromatography. Removal of the bornyl group afforded highly enantiomerically enriched cyclopropanes. An example of the simple conversions of these cyclopropanes into useful cyclopropane α-amino acids is also illustrated. The syntheses of several vinyl selenides and selenones are also described.
Acetoxyselenenylation of Olefins for the Preparation of Vinylic and Allylic Acetates
Engman, Lars
, p. 884 - 890 (2007/10/02)
Terminal and 1,2-disubstituted olefins were irreversibly acetoxyselenenylated by treatment with PhSeBr in an acetate buffer solution.Styrene derivatives yielded only Markovnikov adducts whereas simple terminal olefins and olefins containing an allylic oxygen substituent (acyloxy or aryloxy group) afforded significant amounts (50-85percent) of the anti-Markovnikov isomer.The product mixtures were isomerized to contain 90-97percent of the Markovnikov products by treatment with a catalytic amount (6-41percent) of BF3*OEt2 in chloroform.Oxidation (SO2Cl2/hydrolysis or MCPBA) of the isomerized products and selenoxide elimination at elevated temperature toward the acetoxy group afforded enol acetates in fair yields.The selenoxides of the anti-Markovnikov isomers (unisomerized mixtures) spontaneously eliminated, in the presence of the selenoxides of the Markovnikov isomer, to give allylic acetates in good yields at ambient temperature.
