Application of Crystallization-Induced Asymmetric Transformation to a General, Scalable Method for the Resolution of 2, 8-Disubstituted Tröger's Base Derivatives

…, T Field, MR Schmidt, AK DeStefano…

Index: Jameson, Donald L.; Field, Thomas; Schmidt, Monica R.; Destefano, Alyson K.; Stiteler, Christopher J.; Venditto, Vincent J.; Krovic, Brooke; Hoffman, Christopher M.; Ondisco, Matthew T.; Belowich, Matthew E. Journal of Organic Chemistry, 2013 , vol. 78, # 22 p. 11590 - 11596

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Citation Number: 9

Abstract

A general method for the gram scale resolution of 2-substituted and 2, 8-disubstituted Tröger's base (TB) derivatives in 63–91% yield has been achieved through the application of crystallization-induced asymmetric transformation (CIAT). Enantiomeric ratios of the resolved TB derivatives range from 99.1: 0.9 to> 99.5: 0.5. Among the Tröger's base compounds resolved are four synthetically valuable bromo and iodo derivatives.