Kenji Monde and Tohru Taniguchi and Nobuaki Miura and Charles Santhanaraju Vairappan and Minoru Suzuki (2006) Absolute Configurations of Endoperoxides Determined by Vibrational Circular Dichroism (VCD). Tetrahedron Lett 47:4389. Tetrahedron Letters, 47 (26). pp. 4389-4392. ISSN 0040-4039
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Abstract
Diastereomeric mixture on the peroxide portion of an endoperoxide acetylmajapolene A (1) was efficiently separated by HPLC on a chiral column, submitting to vibrational circular dichroism (VCD) investigation. The ab initio theoretical VCD and IR calculations of 1a and 1b were performed by density functional theory (DFT) using the B3PW91/6-31G(d,p) level of theory. Focusing on an isolated characteristic peroxide vibrational band, absolute configurations of 1a and 1b were unambiguously determined as (1R,4R,7S,10S) and (1S,4S,7S,10S), respectively. This is the first VCD application to endoperoxides which exist abundantly in nature.
| Item Type: | Article |
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| Keyword: | Peroxide; Absolute configuration; Vibrational circular dichroism; VCD; DFT calculation |
| Subjects: | Q Science > QD Chemistry |
| Depositing User: | ADMIN ADMIN |
| Date Deposited: | 15 Oct 2015 16:15 |
| Last Modified: | 12 Oct 2017 12:39 |
| URI: | https://eprints.ums.edu.my/id/eprint/12035 |
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