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Diastereoselectivity control in photosensitized addition of methanol to (R)-(+)-limonene.

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.
AuthorsSang Chul Shim, Dong Suk Kim, Dong Jin Yoo, Takehiko Wada, Yoshihisa Inoue
JournalThe Journal of organic chemistry (J Org Chem) Vol. 67 Issue 16 Pg. 5718-26 (Aug 09 2002) ISSN: 0022-3263 [Print] United States
PMID12153274 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Cyclohexenes
  • Solutions
  • Terpenes
  • Ether
  • Limonene
  • Methanol
Topics
  • Cyclohexenes
  • Ether
  • Limonene
  • Methanol
  • Models, Molecular
  • Molecular Conformation
  • Photochemistry
  • Solutions
  • Spectrometry, Fluorescence
  • Stereoisomerism
  • Structure-Activity Relationship
  • Terpenes

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