Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid using a chiral N-(2-hydroxymethyl-4-pyrrolidinyl)benzamide template

Jun Ichi Mizoguchi, Yuko Kawanami, Takehiko Wada, Kazuya Kodama, Kinsei Anzai, Toshiharu Yanagi, Yoshihisa Inoue

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)

Abstract

(Chemical Equation Presented) Supramolecular enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid (AC) was performed in the presence of (2S,4S)-4-amino-5-chloro-2-methoxy-N-(1-ethyl-2-hydroxymethyl-4- pyrrolidinyl)benzamide (TKS159), and its stereoisomers were employed as chiral templates. The TKS template provides us with a novel hydrogen-bonding and shielding motif for enantioface-selectively binding an AC molecule. Chiral products 2 and 3 were obtained in good enantiomeric excesses (ee's) of 40% and 40%, respectively.

Original languageEnglish
Pages (from-to)6051-6054
Number of pages4
JournalOrganic letters
Volume8
Issue number26
DOIs
Publication statusPublished - 2006 Dec 21
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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