Synthesis and applications of secondary amine derivatives of (+)-dehydroabietylamine in chiral molecular recognition

Organic & Biomolecular Chemistry
Tiina LaaksonenKristiina Wähälä

Abstract

(+)-Dehydroabietylamine (1a), the novel derivatives (2a-6a) and their NTf2 salts (1b-6b) were tested as chiral NMR solvating agents for the resolution of enantiomers of the model compound Mosher's acid (7) and its n-Bu4N salt (8). Best enantiomeric discrimination of 7 was obtained using bisdehydroabietylamino-N(1),N(2)-ethane-1,2-diamine (6a), and of 8 using N-(dehydroabietyl)-2-(dehydroabietylamino)ethanaminium bis((trifluoromethyl)-sulfonyl)-amide (6b). For the maximal resolution of enantiomers of 8, 1.0 eq. of 6b were needed. However, 0.5 eq. of 6a sufficed for the maximal resolution of enantiomers of 7. Enantiomeric excess studies were successfully conducted using 6a and 6b. The capability of 6a and 6b to recognize the enantiomers of various α-substituted carboxylic acids and their n-Bu4N salts were examined. Best resolutions were observed for aliphatic and aromatic carboxylic acids bearing an electronegative α-substituent. Now the ee studies on such non-aromatic carboxylic acids are also feasible.

References

Apr 20, 2010·Angewandte Chemie·Juan A AguilarGareth A Morris
Jun 5, 2013·Topics in Current Chemistry·Gloria Uccello-Barretta, Federica Balzano
Jan 18, 2014·Organic & Biomolecular Chemistry· LokeshN Suryaprakash
Jul 24, 2014·Chemical Communications : Chem Comm·Míriam Pérez-TrujilloTeodor Parella

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Citations

Nov 28, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tiina LaaksonenKristiina Wähälä
Nov 15, 2017·Organic & Biomolecular Chemistry·Suguru ItoMasatoshi Asami
Aug 9, 2019·The Journal of Organic Chemistry·Vincent OrnelisAnnemieke Madder

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