Title
Chiroptical Protocol for the Absolute Configurational Assignment of Alkyl-Substituted Epoxides Using Bis(zinc porphyrin) as a CD-Sensitive Bidentate Host
Author
Shiori Takeda, Satoshi Hayashi, Masahiro Noji, Toshikatsu Takanami
Year
2018
Journal
The Journal of Organic Chemistry
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 Article
Instrument
J-820
Keywords
Circular dichroism, Soret band, Organic chemistry, Stereochemistry, Absolute configuration, Pharmaceutical