Application of dirhodium reagent Rh2(OCOCF3)4 to the determination of the absolute configurations of secondary and tertiary alcohols
10.13220/j.cnki.jipr.2015.06.006
- Author:
Gui-Yang XIA
1
Author Information
1. School of Chinese Materia Medica, Tianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine
- Publication Type:Journal Article
- Keywords:
Absolute configuration;
Circular dichroism Rh2(OCOCF3)4;
Secondary alcohols;
Tertiary alcohols
- From:
Journal of International Pharmaceutical Research
2015;42(6):726-733
- CountryChina
- Language:Chinese
-
Abstract:
The determination of the absolute configuration of natural products has drawn great attention for a long time. The circular dichroism (CD) spectroscopy appears to be an efficient method for determining the absolute configuration of chiral compounds in solution. Studies from abroad indicated a straightforward method which employed a transition metal chelate dirhodium reagent Rh2(OCOCF3)4 for the assignment of the absolute configurations of the secondary and tertiary alcohols. The CD spectra of the in situ complexes of chiral alcohols with Rh2(OCOCF3)4 showed up to 6 Cotton effects (A-F) at the range of 600-270 nm. It was demonstrated that the E band, appearing at ca. 350 nm, can be used for correlation of its sign and the stereochemistry of the secondary or tertiary alcohols, by applying the bulkiness rule. In this review, the methodology including theory, procedures and results, as well as the application examples are presented.
