38944-14-8Relevant articles and documents
A General Approach to Stereospecific Cross-Coupling Reactions of Nitrogen-Containing Stereocenters
Binayeva, Meruyert,Biscoe, Mark R.,Diane, Mohamed,Ma, Xinghua,Ralph, Glenn,Wang, Chao-Yuan,Zhao, Haoran,Zhao, Shibin
supporting information, p. 781 - 791 (2020/03/11)
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Stereocomplementary Synthesis of Pharmaceutically Relevant Chiral 2-Aryl-Substituted Pyrrolidines Using Imine Reductases
Chen, Fei-Fei,Chen, Qi,Li, Bo-Bo,Xu, Jian-He,Zhang, Yu-Hui,Zheng, Gao-Wei,Zhou, Xin-Yi
supporting information, p. 3367 - 3372 (2020/04/21)
Exploring a collection of naturally occurring imine reductases (IREDs) identified two stereocomplementary IREDs with reducing activity toward sterically hindered 2-aryl-substituted pyrrolines. Using (R)-selective ScIR and (S)-selective SvIR, various chiral 2-aryl-substituted pyrrolidines with excellent enantioselectivity (>99% ee) were stereocomplementarily synthesized in good yield (60-80%), demonstrating the feasibility of IREDs for generating pharmaceutically relevant chiral 2-aryl-substituted pyrrolidine intermediates.
Hammett correlation of nornicotine analogues in the aqueous aldol reaction: Implications for green organocatalysis
Rogers, Claude J.,Dickerson, Tobin J.,Brogan, Andrew P.,Janda, Kim D.
, p. 3705 - 3708 (2007/10/03)
(Chemical Equation Presented) A series of meta- and para-substituted 2-arylpyrrolidines were synthesized and examined for their ability to catalyze an aqueous aldol reaction under buffered conditions. Kinetic analysis of arylpyrrolidine-catalyzed reactions displayed a linear Hammett correlation with ρ = 1.14 (R2 = 0.996), indicating that the reaction is accelerated by electron-withdrawing aryl rings. These results show promise for the development of a synthetically viable aqueous organocatalyst.