Absolute asymmetric Strecker synthesis in a mixed aqueous medium: reliable access to enantioenriched α-aminonitrile

Abstract

Under aqueous conditions, total spontaneous resolution of α-aminonitrile occurred by the reaction of three achiral reagents; therefore, absolute asymmetric Strecker synthesis was demonstrated.

Autocatalysis: Kinetics, Mechanisms and Design

“…Later, the same group reported the amplification of a small enantiomeric excess in a similar Strecker reaction by a cyclic temperature regulation that initiates the crystallization-dissolution cycles. [139]…”

Chemical Mechanisms of Prebiotic Chirality Amplification

“…Summarizing the discussion above, we would like to point out that only the models of chirality amplification based on DNLEs, i.e., on asymmetric autocatalysis and asymmetric autoamplification/dynamic chirality control [ 33 , 34 , 42 , 47 ], stand close to the expected conditions for mimicking natural selection in chemical systems [ 55 ]. The DNLE-based models, dealing with far-from-equilibrium chemical systems, operate by analogy with competition-based biological processes (which are fundamentally irreversible) [ 48 , 55 , 56 ], while the models exploiting crystallization-assisted chiral amplification [ 53 , 54 ] or “hyperpositive” nonlinear effects [ 49 ] lack this similarity. From the mathematical perspective, the former chemical systems obey the rules similar to those of natural selection [ 48 , 56 ], which allows one entity (enantiomer), competing for the same chemical stuff, to drive the other competitor out completely and dominate the available space.…”

“…These results demonstrate the possibility of attaining enantiopure product from achiral reactants in a racemoselective reversible catalytic reaction, coupled with precipitation-induced chiral amplification, possibly biased by a minor chiral impurity, without action of any nonlinear effects. More recently, analogous approach has been reproduced in the absolute asymmetric Strecker synthesis of α -aminonitriles in a water-methanol solution [ 54 ]. In the latter case, quasistochastic formation of ( R )- and ( S )-products has been observed (37 vs. 36 times), apparently reflecting the absence of intervention of any external chiral effects.…”

Overview on magnetically recyclable ferrite nanoparticles: synthesis and their applications in coupling and multicomponent reactions

“…156 Since then, signicant amount of the work has been reported in literature for the application of this reaction for the preparation of various racemic as well as chiral a-amino acids, a-amino nitriles and heterocyclic derivatives. [157][158][159][160][161][162][163] Typical mechanism of Strecker synthesis is depicted in Fig. 9.…”