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

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

研究成果: Article査読

19 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)5718-5726
ページ数9
ジャーナルJournal of Organic Chemistry
67
16
DOI
出版ステータスPublished - 2002 8 9
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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