27511-41-7Relevant academic research and scientific papers
The Detosylation of Chiral 1,2-Bis(tosylamides)
Butler, Nicholas M.,Clark, Timothy,Gaston, Jayden J.,Keller, Paul A.,Smyth, Jamie E.,Tague, Andrew J.,Van Eikema Hommes, Nico,Willis, Anthony C.,Yu, Haibo
, p. 9163 - 9180 (2021)
The deprotection of chiral 1,2-bis(tosylamides) to their corresponding 1,2-diamines is mostly unsuccessful under standard conditions. In a new methodology, the use of Mg/MeOH with sufficient steric additions allows the facile synthesis of 1,2-diamines in 78-98% yields. These results are rationalized using density functional theory and the examination of inner and outer-sphere reduction mechanisms.
Ring-opening and -expansion of 2,2′-biaziridine: Access to diverse enantiopure linear and bicyclic vicinal diamines
Bailey, Stephen J.,Wales, Steven M.,Willis, Anthony C.,Keller, Paul A.
, p. 4344 - 4347 (2014/10/16)
The chiral pool-derived 1,1′-ditosyl-2,2′-biaziridine has been established as a valuable building block for the divergent synthesis of enantiopure vicinal diamines. Efficient procedures for the regioselective ring opening of the biaziridine with oxygen, sulfur, nitrogen, and carbon nucleophiles are described. The strategic use of nucleophiles bearing pendant functionality allows further elaboration of the acyclic products to a variety of 2,2′-bicyclic-embedded diamines. Desymmetrization of the biaziridine has also been accomplished via the selective monoaddition of organocuprates.
