1,1′‐Bi(trishomobarrelenyl) – Synthesis and Chiroptic Properties | Zendy

de Meijere Armin | Zendy; Rauch Karsten | Zendy; Schrader Bernhard | Zendy; Brackmann Farina | Zendy; Pfoh Roland | Zendy; Rühl Stephan | Zendy; Katoh Yasunaka | Zendy; Okamoto Yoshio | Zendy; Wodrich Matthew D. | Zendy; Corminboeuf Clémence | Zendy; Schreiner Peter R. | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

1,1′‐Bi(trishomobarrelenyl) – Synthesis and Chiroptic Properties

Author(s) -

de Meijere Armin,

Rauch Karsten,

Schrader Bernhard,

Brackmann Farina,

Pfoh Roland,

Rühl Stephan,

Katoh Yasunaka,

Okamoto Yoshio,

Wodrich Matthew D.,

Corminboeuf Clémence,

Schreiner Peter R.

Publication year - 2009

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200801111

Subject(s) - chemistry , enantiomer , diastereomer , pentane , absolute configuration , yield (engineering) , amine gas treating , enantiomeric excess , stereochemistry , molar ratio , chiral column chromatography , chirality (physics) , crystallography , organic chemistry , enantioselective synthesis , catalysis , materials science , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark , metallurgy

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)

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research