TY - JOUR
T1 - Application of crystallization-induced asymmetric transformation to a general, scalable method for the resolution of 2,8-disubstituted Tröger's base derivatives
AU - Jameson, Donald L.
AU - Field, Thomas
AU - Schmidt, Monica R.
AU - Destefano, Alyson K.
AU - Stiteler, Christopher J.
AU - Venditto, Vincent J.
AU - Krovic, Brooke
AU - Hoffman, Christopher M.
AU - Ondisco, Matthew T.
AU - Belowich, Matthew E.
PY - 2013/11/15
Y1 - 2013/11/15
N2 - 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.
AB - 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.
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U2 - 10.1021/jo401873x
DO - 10.1021/jo401873x
M3 - Article
C2 - 24116701
AN - SCOPUS:84887967108
SN - 0022-3263
VL - 78
SP - 11590
EP - 11596
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 22
ER -