In:
European Journal of Organic Chemistry, Wiley, Vol. 2009, No. 7 ( 2009-03), p. 1048-1052
Kurzfassung:
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 ).(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Materialart:
Online-Ressource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2009:7
DOI:
10.1002/ejoc.200801111
Sprache:
Englisch
Verlag:
Wiley
Publikationsdatum:
2009
ZDB Id:
1475010-7
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