Abstract |
Highly diastereodifferentiating bimolecular asymmetric photoreaction was achieved in the photosensitized polar addition of methanol to ( R)-(+)-limonene. The diastereomeric excess (de) of the photoadduct could be controlled and fine-tuned by changing the internal/external factors such as solvent polarity, reaction temperature, and structure of the sensitizers. The de increased from 23% obtained upon xylene photosensitization in pure methanol at room temperature to >96% upon singlet sensitization with methyl benzoate at -75 degrees C in 0.5 M methanol/ diethyl ether solution.
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Authors | Sang Chul Shim, Dong Suk Kim, Dong Jin Yoo, Takehiko Wada, Yoshihisa Inoue |
Journal | The Journal of organic chemistry
(J Org Chem)
Vol. 67
Issue 16
Pg. 5718-26
(Aug 09 2002)
ISSN: 0022-3263 [Print] United States |
PMID | 12153274
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Chemical References |
- Cyclohexenes
- Solutions
- Terpenes
- Ether
- Limonene
- Methanol
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Topics |
- Cyclohexenes
- Ether
- Limonene
- Methanol
- Models, Molecular
- Molecular Conformation
- Photochemistry
- Solutions
- Spectrometry, Fluorescence
- Stereoisomerism
- Structure-Activity Relationship
- Terpenes
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