64715-88-4Relevant academic research and scientific papers
The dinosyl group: A powerful activator for the regioselective alcoholysis of aziridines
Stanetty, Christian,Blaukopf, Markus K.,Lachmann, Bodo,Noe, Christian R.
supporting information; experimental part, p. 3126 - 3130 (2011/07/08)
The N-2,4-dinitrophenylsulfonyl group (dinosyl, DNs) was found to be an excellent choice for the N-activation of aziridines towards ring cleavage with primary, secondary, andsterically demanding tertiary alcohols. Alcoholysis does not need any additional
Recent progress using chiral formamidines in asymmetric syntheses
Meyers
, p. 2589 - 2612 (2007/10/02)
The ability to generate a carbanion next to nitrogen in a chiral environment has led to a number of useful asymmetric routes to alkaloids and related substances. Mechanistic studies have been conducted to understand the nature of these alkylations.
Synthesis, Regioselective Deprotonation, and Stereoselective Alkylation of Fluoro Ketimines
Welch, John T.,Seper, Karl W.
, p. 2991 - 2999 (2007/10/02)
Fluoroacetone imines of cyclohexylamine, valinol O-methyl ether, and phenylalaninol O-methyl ether and 2-fluorocyclohexanone imines of cyclohexylamine and phenylalaninol O-methyl ether were prepared.The temperature-dependent, regioselective deprotonation of these imines was employed in highly regioselective alkylation reactions.The deprotonation of fluoroacetone cyclohexylimine on the carbon bearing fluorine yielded only a single stereoisomer as determined by low temperature 19F NMR.In contrast, deprotonation of fluoroacetone O-benzyloximes was not regiospecific under any of the conditions examined.
Asymmetric Induction Reactions. I. Asymmetric Sigmatropic Rearrangements of Sulfur Ylides Derived from Chiral Ketenimines and Trimethylsulfonium Ylide
Hiroi, Kunio,Sato, Shuko
, p. 2331 - 2338 (2007/10/02)
The asymmetric (2,3) sigmatropic rearrangements of 2-alkylamino-3-phenyl-2-pentenyl-methylsulfonium methylides were accomplished by the reaction of ethylphenylketenimines 3 having a chiral carbon next to the nitrogen atom with trimethylsulfonium ylide, and acidic hydrolysis of the imines 4 thus obtained led to optically active 3-methylthiomethyl-3-phenyl-2-pentanone (5).The reaction of ethylphenylketene (-)-menthylimine (3g) with trimethylsulfonium ylide at -78 deg C resulted in the highest optical yield of (R)-(-)-5 in the above sequence.Keywords--asymmetric induction; (2,3) sigmatropic rearrangement; chiral ketenimine; sulfur ylide; trimethylsulfonium ylide
ASYMMETRIC CONJUGATE ADDITION OF COPPER AZAENOLATES AS SYNTHETIC EQUIVALENT OF ENOLATES TO CYCLIC ENONES
Yamamoto, Keiji,Iijima, Masayuki,Ogimura, Yoshinobu
, p. 3711 - 3714 (2007/10/02)
Asymmetric conjugate addition to prochiral cyclic enones was devised by using copper azaenolates derived from an acetone imine of optically active amino ethers which were prepared from α-amino acids, the optical yields of the resulting 3-acetonylcycloalkanones being found to attain as high as 75percent e.e.
