129879-90-9Relevant academic research and scientific papers
Dynamic asymmetric multicomponent resolution: Lipase-mediated amidation of a double dynamic covalent system
Vongvilai, Pornrapee,Ramstroem, Olof
supporting information; experimental part, p. 14419 - 14425 (2010/02/16)
The Strecker reaction is one of the most important multicomponent reactions developed, leading to R-aminonitriles that are versatile substrates for many synthetic applications. In the present study, this reaction type has been applied to a double dynamic covalent resolution protocol, leading to efficient C-C- and C-N-bond generation as well as chiral discrimination. The combination of transimination with iminecyanation enabled the dynamic exchange in more than one direction around a single stereogenic center of restricted structure. This multiple exchange process could generate a vast range of compounds from a low number of starting materials in very short time. The resulting double dynamic covalent systems, created under thermodynamic control, were subsequently coupled in a one-pot process with kinetically controlled lipase-mediated transacylation. This resulted in complete resolution of the dynamic systems, yielding the optimal N-acyl-α-aminonitriles for the enzyme, where the individual chemoenzymatic reactions could produce enantiomerically pure acylated N-substituted α-aminonitriles in good yields.
