Inherently Chiral Resorcin[4]arenes with Urea and Amide Side Arms: Synthesis, Structure and Chiral Recognition

Wiegmann S, Fukuhara G, Neumann B, Stammler H-G, Inoue Y, Mattay J (2013)
European Journal Of Organic Chemistry 2013(7): 1240-1245.

Journal Article | Published | English

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Abstract
Starting from an inherently chiral aminomethyl-substituted resorcin[4]arene, a series of urea and amide derivatives were synthesized; these new functionalities extend the macrocycle cavity and introduce new opportunities for chiral recognition. A pair of diastereomeric macrocycles was obtained by introducing (S)-(-)-1-phenylethyl-urea functionalities. Chiral recognition capabilities of the diastereomeric hosts were investigated by circular dichroism spectral titration to reveal modest R/S selectivities of up to 1.4 for mandelic acid and other related carboxylic guests.
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Wiegmann S, Fukuhara G, Neumann B, Stammler H-G, Inoue Y, Mattay J. Inherently Chiral Resorcin[4]arenes with Urea and Amide Side Arms: Synthesis, Structure and Chiral Recognition. European Journal Of Organic Chemistry. 2013;2013(7):1240-1245.
Wiegmann, S., Fukuhara, G., Neumann, B., Stammler, H. - G., Inoue, Y., & Mattay, J. (2013). Inherently Chiral Resorcin[4]arenes with Urea and Amide Side Arms: Synthesis, Structure and Chiral Recognition. European Journal Of Organic Chemistry, 2013(7), 1240-1245.
Wiegmann, S., Fukuhara, G., Neumann, B., Stammler, H. - G., Inoue, Y., and Mattay, J. (2013). Inherently Chiral Resorcin[4]arenes with Urea and Amide Side Arms: Synthesis, Structure and Chiral Recognition. European Journal Of Organic Chemistry 2013, 1240-1245.
Wiegmann, S., et al., 2013. Inherently Chiral Resorcin[4]arenes with Urea and Amide Side Arms: Synthesis, Structure and Chiral Recognition. European Journal Of Organic Chemistry, 2013(7), p 1240-1245.
S. Wiegmann, et al., “Inherently Chiral Resorcin[4]arenes with Urea and Amide Side Arms: Synthesis, Structure and Chiral Recognition”, European Journal Of Organic Chemistry, vol. 2013, 2013, pp. 1240-1245.
Wiegmann, S., Fukuhara, G., Neumann, B., Stammler, H.-G., Inoue, Y., Mattay, J.: Inherently Chiral Resorcin[4]arenes with Urea and Amide Side Arms: Synthesis, Structure and Chiral Recognition. European Journal Of Organic Chemistry. 2013, 1240-1245 (2013).
Wiegmann, Sebastian, Fukuhara, Gaku, Neumann, Beate, Stammler, Hans-Georg, Inoue, Yoshihisa, and Mattay, Jochen. “Inherently Chiral Resorcin[4]arenes with Urea and Amide Side Arms: Synthesis, Structure and Chiral Recognition”. European Journal Of Organic Chemistry 2013.7 (2013): 1240-1245.
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