119405-95-7Relevant articles and documents
Trans-Symmetric Dynamic Covalent Systems: Connected Transamination and Transimination Reactions
Schaufelberger, Fredrik,Hu, Lei,Ramstr?m, Olof
, p. 9776 - 9783 (2015)
The development of chemical transaminations as a new type of dynamic covalent reaction is described. The key 1,3-proton shift is under complete catalytic control and can be conducted orthogonally to, or simultaneous with, transimination in the presence of an amine to rapidly yield two-dimensional dynamic systems with a high degree of complexity evolution. The transamination-transimination systems are proven to be fully reversible, stable over several days, compatible with a range of functional groups, and highly tunable. Kinetic studies show transamination to be the rate-limiting reaction in the network. Furthermore, it was discovered that readily available quinuclidine is a highly potent catalyst for aldimine transaminations. This study demonstrates how connected dynamic reactions give rise to significantly larger systems than the unconnected counterparts, and shows how reversible isomerizations can be utilized as an effective diversity-generating element. Constant exchange: The development of chemical transaminations as a new type of dynamic covalent reactions is described (see figure). This study demonstrates how connected dynamic reactions give rise to significantly larger systems than the unconnected counterparts, and shows how reversible isomerizations can be utilized as an effective diversity-generating element.
Scandium triflate catalyzed cycloaddition of imines with 1,1-cyclopropanediesters: Efficient and diastereoselective synthesis of multisubstituted pyrrolidines
Kang, Yan-Biao,Tang, Yong,Sun, Xiu-Li
, p. 299 - 301 (2007/10/03)
A tandem ring-opening-cyclization reaction of cyclopropanes with imines in the presence of 5 mol% of scandium triflate was developed for the highly diastereoselective synthesis of multisubstituted pyrrolidines. The Royal Society of Chemistry 2006.
Cycloaddition of (N-Alkyl-N-phenylamino)ketene with Imines
Brady, William T.,Dad, Mohammad M.
, p. 6118 - 6122 (2007/10/02)
(N-Alkyl-N-phenylamino)ketenes were prepared in the presence of various imines, and a cycloaddition reaction occurred to yield 3-(N-alkyl-N-phenylamino)-2-azetidinones.The size and electronic nature of the imine substituents were varied in order to probe those factors that influence the stereochemistry of the cycloaddition.The stereochemistry of the 2-azetidinone was determined by the substitution pattern of the imines.In general, the stereochemistry of the 2-azetidinone products are significantly influenced by the bulk of the N substituent on the imine.These results are discussed in terms of a two-step zwitterionic intermediate.
