Chiroptical Protocol for the Absolute Configurational Assignment of Alkyl-Substituted Epoxides Using Bis(zinc porphyrin) as a CD-Sensitive Bidentate Host.
J Org Chem
; 84(2): 645-652, 2019 Jan 18.
Article
in En
| MEDLINE
| ID: mdl-30547578
ABSTRACT
The absolute configurations of simple alkyl-substituted chiral epoxides not bearing other ligating groups are readily determined via the exciton-coupled circular dichroism (ECCD) protocol using bidentate bis(zinc porphyrin) host system BP1 as a CD-sensitive chirality probe. In this situation, chiral epoxides can successfully be incorporated into the cleft of V-shaped host BP1 by double coordination of both oxygen lone pairs of the guest to the two central zinc ions of the host. We also propose a working model based on an MM2 optimized structure of the substrates that enables nonempirical prediction of the chirality of the bound epoxide.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Type of study:
Diagnostic_studies
/
Prognostic_studies
Language:
En
Journal:
J Org Chem
Year:
2019
Document type:
Article
Affiliation country:
Japan