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Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Tröger’s Base Derivatives: Part II
Author(s) -
BenkhäuserSchunk Christian,
Wezisla Boris,
Urbahn Kirstin,
Kiehne Ulf,
Daniels Jörg,
Schnakenburg Gregor,
Neese Frank,
Lützen Arne
Publication year - 2012
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201200029
Subject(s) - derivative (finance) , absolute configuration , chemistry , circular dichroism , enantiomer , base (topology) , crystal structure , chiral resolution , phase (matter) , stereochemistry , combinatorial chemistry , crystallography , organic chemistry , mathematical analysis , mathematics , financial economics , economics
Seven racemic derivatives of Tröger’s base—the 1,7‐dibromo‐substituted derivative 3 , the 2,8‐dibromo‐substituted derivative 4 , the 2,8‐diiodo‐substituted derivative 5 , the 3,9‐diiodo‐substituted derivative 6 , the 4,10‐dibromo‐substituted derivative 7 , its singly debrominated analogue 8 , and the 2,8‐diamino‐substituted derivative 9 in its Fmoc‐protected form—were synthesized and successfully resolved by (recycling) HPLC on a stationary Whelk‐O1 phase at a semipreparative scale. These are valuable functionalized C 2 ‐symmetric building blocks for further applications. Their absolute configurations were determined by X‐ray crystal structure analysis and/or by comparison of their quantum chemically calculated circular dichroism and UV/Vis spectra with the experimental obtained spectra.