187532-11-2Relevant academic research and scientific papers
Selective synthesis of cis-2-vinyl-3-alkylaziridines and 3-pyrrolines from common intermediates (Z)-4-N-arylsulfonylaminoalk-2-en-1-ols
Ishii, Kiyonori,Ohno, Hiroaki,Takemoto, Yoshiji,Osawa, Eriko,Yamaoka, Yumiko,Fujii, Nobutaka,Ibuka, Toshiro
, p. 2155 - 2163 (2007/10/03)
A simple method for the synthesis of both cis-2-vinylaziridines and 3-pyrrolines from common intermediate (Z)-4-(N-arylsulfonyl)amino-4-alkylbut-2-en-1-ols, is described. Palladium(0)-catalyzed reactions of methyl carbonates of the N-protected (Z)-4-amino-4-alkylbut-2-en-1-ols yield predominantly cis-3-alkyl-2-vinylaziridines. Alternatively, upon exposure to sodium hydride, methanesulfonates derived from N-protected (Z)-4-amino-4-alkylbut-2-en-1-ols give exclusively the corresponding 3-pyrrolines in high yields. A synthesis of biologically important (S)-3,4-dehydroproline is also presented.
Selective synthesis of nonracemic 3-pyrrolines and 2,3-cis-2-vinylaziridines from (z)-amino allylic alcohols: a new synthetic route to chiral 3,4-dehydroproline
Ishii, Kiyonori,Ohno, Hiroaki
, p. 228 - 230 (2007/10/03)
Both nonracemic 3-pyrrolines and 2,3-cis-2-vinyIaziridines have been synthesized selectively from common (Z)-allylic alcohols by simply changing the leaving group and the reaction conditions. Whereas treatment of (Z)-allylic mesylates with NaH yields exclusively 3-pyrrolines in high yields, exposure of allylic methyl carbonates to a catalytic amount of Pd(PPh3)4 affords 2,3-cw-2-vinylaziridines diastereoselectively in high yields. A simple synthesis of (5)-3,4-dehydroproline starting from (/?)-serine is also described. Thieme Stuttgart.
A 2,3-cis-selective synthesis of aziridines bearing a vinyl group from allyl methyl carbonates and allyl mesylates
Ohno, Hiroaki,Ishii, Kiyonori,Honda, Asami,Tamamura, Hirokazu,Fujii, Nobutaka,Takemoto, Yoshiji,Ibuka, Toshiro
, p. 3703 - 3716 (2007/10/03)
A convenient method for the synthesis of synthetically useful chiral 2-vinylaziridines from natural α-amino acids is described. Satisfactory 2,3-cis-selectivities are obtained by exposure of methyl carbonates of various allylic alcohols bearing an N-protected amino group to a catalytic amount of tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4, in aprotic solvents such as THF. Base-promoted aziridination of mesylates of various N-protected amino allylic alcohols followed by Pd(PPh3)4 catalyzed isomerization for the 2,3-cis-selective synthesis of vinylaziridines is also presented.
A Thermodynamic Preference of Chiral N-Methanesulfonyl and N-Arenesulfonyl 2,3-cis-3-Alkyl-2-Vinylaziridines over Their 2,3-Trans-Isomers: Useful Palladium(0)-Catalyzed Equilibration Reactions for the Synthesis of (E)-Alkene Dipeptide Isosteres
Ibuka, Toshiro,Mimura, Norio,Aoyama, Hiroshi,Akaji, Masako,Ohno, Hiroaki,Miwa, Yoshihisa,Taga, Tooru,Nakai, Kazuo,Tamamura, Hirokazu,Fujii, Nobutaka,Yamamoto, Yoshinori
, p. 999 - 1015 (2007/10/03)
Palladium(0)-catalyzed reactions of N-methanesulfonyl- or N-(arenesulfonyl)-3-alkyl-2-vinylaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations. A highly stereoselective synthetic route to (E)-alkene dipeptide isosteres having desired stereochemistries from 2,3-cis-3-isobutyl-2-vinylaziridine by the use of organocopper chemistry is also presented.
An unusual thermodynamic preference of chiral N-arylsulfonyl cis-3-alkyl-2-vinylaziridines over their trans-isomers: Palladium(0)-catalysed equilibration reactions
Mimura, Norio,Ibuka, Toshiro,Akaji, Masako,Miwa, Yoshihisa,Taga, Tooru,Nakai, Kazuo,Tamamura, Hirokazu,Fujii, Nobutaka,Yamamoto, Yoshinori
, p. 351 - 352 (2007/10/03)
Palladium (0)-catalysed reactions of N-alkylsulfonyl- or N-arylsulfonyl-3-alkyl-2-vinylaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations.
