Enantiodifferentiating photocyclodimerization of cyclohexa-1,3-diene sensitized by chiral arenecarboxylates

Sadayuki Asaoka, Motohiro Ooi, Peiyun Jiang, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The enantiodifferentiating photosensitized cyclodimerization of cyclohexa-1,3-diene 1 was performed over a range of temperatures in the presence of chiral arene(poly)carboxylates, giving endo- and exo-[4 + 2] cyclodimers (2a, 2b) and anti- and syn-[2 + 2] cyclodimers (3a, 3b). Among the three chiral cyclodimers (2a, 2b, 3a), only 2b was obtained as an optically active species with an enantiomeric excess (ee) of up to 8.2%. The detailed reaction mechanism and the origin of the enantiodifferentiation have been elucidated, and the crucial role played by the 'microenvironmental polarity' around the chromophore in determining the photoreactivity and the ee of the product is also discussed.

Original languageEnglish
Pages (from-to)77-84
Number of pages8
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number1
Publication statusPublished - 2001 Dec 1
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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