Application of crystallization-induced asymmetric transformation to a general, scalable method for the resolution of 2,8-disubstituted Tröger's base derivatives

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 fr...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-11, Vol.78 (22), p.11590-11596
Main Authors: 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
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo401873x