Journal article

Publication year: 2009

Pages: 1048-1052

Journal: European Journal of Organic Chemistry

Volume number: 2009

Issue number: 7

DOI Link: https://doi.org/10.1002/ejoc.200801111

Publisher: Wiley

Abstract: 

1,1′‐Bi(endo,exo,syn‐pentacyclo[3.3.3.0^2,4.0^6,8.0^9,11]undecyl)[1,1′‐bi(trishomobarrelenyl)] (4) has been prepared as a 1:1 mixture of its meso‐ and d,l‐diastereomers in six steps from trishomobarrelene 1 via the amine 5, the N,N′‐bis(trishomobarrelenyl)sulfamide 6 and the 1,2‐(trishomobarrelenyl)diazene 7 in 16 % overall yield. Crystals of meso‐4
were grown from a pentane solution of the mixture and subjected to an
X‐ray structure analysis. The (+)‐ and the (–)‐enantiomer were isolated
by HPLC on a chiral‐phase column. They exhibited significantly enhanced
molar optical rotations which are consistent with the presence of three
helically arranged 1,2‐dicyclopropylethane units in their skeletons. The
absolute configuration of the (+)‐enantiomer was assigned on the basis
of DFT computed optical rotations of both enantiomers to be all‐(S).

Harvard Citation style: de Meijere, A., Rauch, K., Schrader, B., Brackmann, F., Pfoh, R., Rühl, S., et al. (2009) 1,1′‐Bi(trishomobarrelenyl) – Synthesis and Chiroptic Properties, European Journal of Organic Chemistry, 2009(7), pp. 1048-1052. https://doi.org/10.1002/ejoc.200801111

APA Citation style: de Meijere, A., Rauch, K., Schrader, B., Brackmann, F., Pfoh, R., Rühl, S., Katoh, Y., Okamoto, Y., Wodrich, M., Corminboeuf, C., & Schreiner, P. (2009). 1,1′‐Bi(trishomobarrelenyl) – Synthesis and Chiroptic Properties. European Journal of Organic Chemistry. 2009(7), 1048-1052. https://doi.org/10.1002/ejoc.200801111