127022-47-3Relevant articles and documents
Chemoselectivity control in the reactions of 1,2-cyclic sulfamidates with amines
Mata, Lara,Avenoza, Alberto,Busto, Jesús H.,Peregrina, Jesús M.
, p. 6831 - 6839 (2013/06/27)
Although 1,2-cyclic sulfamidates derived from α-methylisoserine undergo nucleophilic displacement at the quaternary center, to the best of our knowledge their behavior with amines as nucleophiles has never been explored. We have found that a broad range of amines can be used, demonstrating the scope of the reaction, and that excellent control of the chemoselectivity can be achieved. Application of this methodology for the synthesis of a chiral α,β-diamino acid and an important piperazinone heterocycle is also presented. Additionally, we have found that DMF and DMSO behave not only as polar aprotic solvents but also as O-nucleophilic reagents, allowing the incorporation of an oxygen atom at a quaternary center of the electrophile, with inversion of configuration. Copyright
SN2 vs. E2 on quaternary centres: An application to the synthesis of enantiopure β2,2-amino acids
Avenoza, Alberto,Busto, Jesus H.,Corzana, Francisco,Jimenez-Oses, Gonzalo,Peregrina, Jesus M.
, p. 980 - 981 (2007/10/03)
SN2 and E2 competing reactions in cyclic sulfamidates can be modulated by the change of an amide group to an ester group attached to the quaternary carbon activated for the nucleophilic attack, allowing an easy approach to enantiopure α,α-disub
Palladium(0)-Catalyzed Amination of Allylic Acetate with Methyl Carbamate
Takagi, Masatoshi,Yamamoto, Keiji
, p. 2123 - 2124 (2007/10/02)
Methyl sodiocarbamate, a recalcitrant nucleophile toward ?-allylpalladium intermediate, was found to react with allylic acetates to give allylic carbamates in the presence of a catalytic amount of Pd(PPh3)4 in THF-DMSO mixed solvent.