131141-50-9Relevant academic research and scientific papers
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.
Iodocyclization of the (Tolylsulfonyl)- and (Trichloroacetyl)carbamates of Secondary α-Allenic Alcohols. Highly Diastereoselective Synthesis of syn-1,2-Amino Alcohols and trans-5-Alkyl-1-oxo-2-oxazolidine-4-carboxylic Acids
Friesen, Richard W.,Kolaczewska, Aleksandra E.
, p. 4888 - 4895 (2007/10/02)
The iodocyclization of tosyl- and (trichloroacetyl)carbamates 9 and 10, respectively, of secondary α-allenic alcohols is described.The cyclofunctionalization reactions are highly diastereoselective, providing trans-5-alkyl-4-(1-iodoethylene)-2-oxazolidino
A HIGHLY STEREOSELECTIVE CONVERSION OF α-ALLENIC ALCOHOLS TO 1,2-SYN AMINO ALCOHOL DERIVATIVES VIA IODOCARBAMATION
Friesen, Richard W.
, p. 4249 - 4252 (2007/10/02)
The iodocarbamation of α-allenic alcohol O-carbamates is described.Reactions carried out in anhydrous Et2O are highly diastereoselective, providing the cyclic carbamates trans-8 and cis-9 in ratios ranging from 21:1 to >99:1.Hydrolysis and acetylation pr
