Asymmetric transformation (deracemisation) of an atropisomeric bisheterocyclic amine

Authors
Coogan, MP Hibbs, DE Smart, E
Citation
Mp. Coogan et al., Asymmetric transformation (deracemisation) of an atropisomeric bisheterocyclic amine, CHEM COMMUN, (19), 1999, pp. 1991-1992
Citations number
15
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
19
Year of publication
1999
Pages
1991 - 1992
Database
ISI
SICI code
1359-7345(19991007):19<1991:AT(OAA>2.0.ZU;2-P
Abstract
Heating (+/-)-6,8,14,17-tetrahydro-7H-[1,2,5]triazepino[3,2-b:7,1-b']diquin azoline-14,17-dione 1 with (+)-CSA gives (-)-1 with > 90% ee via a crystall isation-induced asymmetric transformation, the first non-racemic example of a C-2 symmetric bisheterocycle which is atropisomeric by virtue of retarde d rotation around an N-N bond.