Cavity-extended inherently chiral resorein[4]arenes: Synthesis and chiroptical properties of the cycloenantiomers

Paletta M, Klaes M, Neumann B, Stammler H-G, Grimme S, Mattay J (2008)
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2008(3): 555-562.

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Abstract
Inherently chiral resorcin[4]arenes 2 and 3 were prepared from enantiomerically pure C-4-symmetric rccc-2,8,14,20-tetraisobutyl-4,10,16,22-tetra-O-methylresorcin[4]arene (1). The four 2-bromobenzyl ether residues in precursor 2 were introduced as halide moieties to partake in an intramolecular Pd-catalysed C-C cross-coupling reaction to give tetrabiaryl ether compound 3. The absolute configurations could be derived from the starting compounds and were assigned as (M,R)-(-)-2 and (PS)-(+)-2 for the tetrakis(2'-bromobenzyl) ether compounds as well as (M,R)-(-)-3 and (PS)-(+)-3 for the cavity-extended resorcinarenes. The carbon scaffold of 3 contains four new stereogenic axes whose configurations were assigned by single-crystal X-ray analysis. The simulation of the CD spectra by time-dependent Pariser-Parr-Pople calculations (TDPPP) based on the X-ray data gave very good images of the experimental spectra. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
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Paletta M, Klaes M, Neumann B, Stammler H-G, Grimme S, Mattay J. Cavity-extended inherently chiral resorein[4]arenes: Synthesis and chiroptical properties of the cycloenantiomers. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2008;2008(3):555-562.
Paletta, M., Klaes, M., Neumann, B., Stammler, H. - G., Grimme, S., & Mattay, J. (2008). Cavity-extended inherently chiral resorein[4]arenes: Synthesis and chiroptical properties of the cycloenantiomers. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008(3), 555-562.
Paletta, M., Klaes, M., Neumann, B., Stammler, H. - G., Grimme, S., and Mattay, J. (2008). Cavity-extended inherently chiral resorein[4]arenes: Synthesis and chiroptical properties of the cycloenantiomers. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2008, 555-562.
Paletta, M., et al., 2008. Cavity-extended inherently chiral resorein[4]arenes: Synthesis and chiroptical properties of the cycloenantiomers. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008(3), p 555-562.
M. Paletta, et al., “Cavity-extended inherently chiral resorein[4]arenes: Synthesis and chiroptical properties of the cycloenantiomers”, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2008, 2008, pp. 555-562.
Paletta, M., Klaes, M., Neumann, B., Stammler, H.-G., Grimme, S., Mattay, J.: Cavity-extended inherently chiral resorein[4]arenes: Synthesis and chiroptical properties of the cycloenantiomers. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2008, 555-562 (2008).
Paletta, Marlene, Klaes, Michael, Neumann, Beate, Stammler, Hans-Georg, Grimme, Stefan, and Mattay, Jochen. “Cavity-extended inherently chiral resorein[4]arenes: Synthesis and chiroptical properties of the cycloenantiomers”. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2008.3 (2008): 555-562.
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