138212-40-5Relevant academic research and scientific papers
syn-1,2-amino alcohols via diastereoselective allylic C-H amination
Fraunhoffer, Kenneth J.,White, M. Christina
, p. 7274 - 7276 (2008/02/06)
A novel Pd/sulfoxide catalyzed diastereoselective allylic C-H amination reaction of chiral homoallylic N-tosyl carbamates is reported. Densely oxygenated ∞-olefin substrates with multiple stereogenic centers undergo allylic C-H amination in excellent yiel
Silver(I)-catalyzed aminocyclization of 2,3-butadienyl and 3,4-pentadienyl carbamates: An efficient and stereoselective synthesis of 4-vinyl-2-oxazolidinones and 4-vinyltetrahydro-2H-1,3-oxazin-2-ones
Kimura,Tanaka,Tamaru
, p. 1689 - 1705 (2007/10/02)
Silver(I) salts in combination with an appropriate base (mostly triethylamine) catalyzed the aminocyclization of N-substituted 2,3-butadienyl carbamates 1 (benzene, 50°C) to provide 4-vinyl-2-oxazolidinones 2 in good yields. The stereoselectivity (trans-2/cis-2) ranged from 1.4 for C5-Me to >30 for C5-phenyl, isopropenyl, and t-butyl derivatives. 3,4-Pentadienyl tosylcarbamates 3, the one-carbon higher homologues of 1, underwent a similar cyclization to give 4-vinyltetrahydro-2H-1,3-oxazin-2-one 4 in synthetically useful yields and in higher trans selectivities than 1.
Silver(I) Catalyzed Amino Cyclization of O-(2,3-Butadienyl) Carbamates: An Efficient and Stereoselective Synthesis of 4-Vinyl-2-oxazolidinones
Kimura, Masanari,Fugami, Keigo,Tanaka, Shuji,Tamaru, Yoshinao
, p. 6359 - 6362 (2007/10/02)
Silver(I) salts catalyze an amino cyclization of O-(2,3-butadienyl) N-tosyl-carbamates to provide mixtures of cis and trans-5-substituted N-tosyl-4-vinyl-2-oxazolidinones, the trans-isomers predominantly or exclusively.
