Synthesis and resolution of naphthyl-Troger's base

Authors
Talas, E Margitfalvi, J Machytka, D Czugler, M
Citation
E. Talas et al., Synthesis and resolution of naphthyl-Troger's base, TETRAHEDR-A, 9(23), 1998, pp. 4151-4156
Citations number
26
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
9
Issue
23
Year of publication
1998
Pages
4151 - 4156
Database
ISI
SICI code
0957-4166(199812)9:23<4151:SARONB>2.0.ZU;2-M
Abstract
A naphthyl analogue of Troger's base {8H, 16H-7,15-methanodinaphtho[2,1-b][ 2',1'-f] [1,5]-diazocine (NTB)} was prepared and successfully resolved usin g (-)- and (+)-di-p-toluoyl-tartaric acid. Enantiomers obtained show extrem ely high specific rotations related to (i) the rigid [1,5]-diazocine skelet on with molecular asymmetry and (ii) the presence of condensed aromatic rin gs, similar to helicenes. (C) 1998 Elsevier Science Ltd. AII rights reserve d.