138212-47-2

Upstream product

• 607729-94-2 1-methyl-2,3-pentadienyl tosylcarbamate 
• 3031-66-1 racem. hex-3-yne-2,5-diol 
• 7319-23-5 (E)-3-hexene-2,5-diol 
• 4083-64-1 Tosyl isocyanate 
• 130690-76-5 meso-(Z)-hex-3-ene-2,5-diol 
• 98758-79-3 (E)-3-hexene-2,5-diol 
• 7319-23-5 dl-(Z)-hex-3-ene-2,5-diol 

Relevant academic research and scientific papers

Stereodivergent Approach to β-Hydroxy α-Amino Acids from C2-Symmetrical Alk-2-yne-1,4-diols

(Matrix Presented) A new stereodivergent route to erythro- and threo-β-substituted serines from a common C2-symmetrical alk-2-yne-1,4-diol is described. Stereocontrol in such an acyclic system is achieved by taking advantage of symmetry. Stereo

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

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

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.