495381-15-2Relevant academic research and scientific papers
Reactivity of cyclic sulfamidates towards lithium acetylides: Synthesis of alkynylated amines
Eskici, Mustafa,Karanfil, Abdullah,?zer, M. Sabih,Sarikürkcü, Cengiz
scheme or table, p. 6336 - 6341 (2011/12/22)
A synthetically useful level of reactivity of cyclic sulfamidates toward acetylides is described. Ring-opening reactions of a structurally diverse set of 1,2-and 1,3-cyclic sulfamidates with a range of lithium acetylides from aliphatic, cyclic, aromatic, heteroaromatic, and functionalized alkynes proceed smoothly in a regioselective manner to give the corresponding N-sulfate intermediates. Hydrolysis of these intermediates under acidic conditions furnishes the alkynylated amines in yields ranging from 29% to 98%. The scope of the acetylenic substitution reaction with the structural variations in both the cyclic sulfamidates and alkynes is briefly examined.
Hetero Diels-Alder reactions of nitroso alkenes with alkoxyallene derivatives bearing carbohydrate auxiliaries: Asymmetric synthesis of 6H-1,2-oxazines and subsequent reductive transformations
Zimmer, Reinhold,Orschel, Beate,Scherer, Stefan,Reissig, Hans-Ulrich
, p. 1553 - 1563 (2007/10/03)
Alkoxyallene derivatives 1a-f bearing carbohydrate auxiliaries at the oxygen were examined in asymmetric hetero Diels-Alder reactions with nitroso alkenes. Diacetoneglucose derived compound aa turned out to be the best precursor furnishing the primary cyc
