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

Sang Chul Shim, Dong Suk Kim, Dong Jin Yoo, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

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°C in 0.5 M methanol/diethyl ether solution.

Original languageEnglish
Pages (from-to)5718-5726
Number of pages9
JournalJournal of Organic Chemistry
Volume67
Issue number16
DOIs
Publication statusPublished - 2002 Aug 9
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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