First synthesis, isolation and characterization of enantiomerically pure and inherently chiral resorc[4]arenes by Lewis acid cyclization of a resorcinol monoalkyl ether

Klaes M, Agena C, Kohler M, Inoue M, Wada T, Inoue Y, Mattay J (2003)
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (8): 1404-1409.

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Abstract
Cyclization of resorcinol monoalkyl ethers with aliphatic aldehydes leads to the corresponding racemic mixtures of C-4-symmetric rccc-resorc[4]arenes. Separation of these isomers was achieved by mono-O-functionalization of the rccc-2,8,14,20-tetramethylresorc[4]arene (2) with (S)-(+)-10-camphorsulfonyl chloride leading to a diastereomeric mixture of (+)-5a and (-)-5b. After removal of the chiral auxiliary the inherently chiral pure enantiomers (+)-2 and (-)-2 were obtained. Further enantiomerically pure rccc-resorc[4]arenes were obtained by cyclization of (+)-3-[(2S)-2-methylbutoxy]-phenol (6) followed by chromatographic separation. The resulting diastereomeric resorc[4]arenes (+)-7a and (-)-7b were examined by CD spectroscopy, showing a perfect mirror image in all solvents examined. This indicates that the resorcarene cavities of (+)-7a and (-)-7b are essentially enantiomers of each other. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
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Klaes M, Agena C, Kohler M, et al. First synthesis, isolation and characterization of enantiomerically pure and inherently chiral resorc[4]arenes by Lewis acid cyclization of a resorcinol monoalkyl ether. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2003;(8):1404-1409.
Klaes, M., Agena, C., Kohler, M., Inoue, M., Wada, T., Inoue, Y., & Mattay, J. (2003). First synthesis, isolation and characterization of enantiomerically pure and inherently chiral resorc[4]arenes by Lewis acid cyclization of a resorcinol monoalkyl ether. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(8), 1404-1409.
Klaes, M., Agena, C., Kohler, M., Inoue, M., Wada, T., Inoue, Y., and Mattay, J. (2003). First synthesis, isolation and characterization of enantiomerically pure and inherently chiral resorc[4]arenes by Lewis acid cyclization of a resorcinol monoalkyl ether. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1404-1409.
Klaes, M., et al., 2003. First synthesis, isolation and characterization of enantiomerically pure and inherently chiral resorc[4]arenes by Lewis acid cyclization of a resorcinol monoalkyl ether. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (8), p 1404-1409.
M. Klaes, et al., “First synthesis, isolation and characterization of enantiomerically pure and inherently chiral resorc[4]arenes by Lewis acid cyclization of a resorcinol monoalkyl ether”, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, pp. 1404-1409.
Klaes, M., Agena, C., Kohler, M., Inoue, M., Wada, T., Inoue, Y., Mattay, J.: First synthesis, isolation and characterization of enantiomerically pure and inherently chiral resorc[4]arenes by Lewis acid cyclization of a resorcinol monoalkyl ether. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 1404-1409 (2003).
Klaes, M, Agena, C, Kohler, M, Inoue, M, Wada, T, Inoue, Y, and Mattay, Jochen. “First synthesis, isolation and characterization of enantiomerically pure and inherently chiral resorc[4]arenes by Lewis acid cyclization of a resorcinol monoalkyl ether”. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 8 (2003): 1404-1409.
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