Remarkable solvent effect on the enantioface selectivity in the Diels- Alder reaction catalyzed by an aluminum complex of a newly prepared chiral menthol derivative

Go Naraku, Kiyoto Hori, Yoshio Ito, Tsutomu Katsuki

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17 Citations (Scopus)

Abstract

Reversal of enantioface selectivity was observed by merely switching the solvent from CH2Cl2 (enantiomer ratio of the adduct = 91:9) to THF (14:86) in the asymmetric Diels-Alder reaction catalyzed by the aluminum complex of a newly prepared chiral menthol derivative. Negative nonlinear effect on the relationship between enantiomeric excesses of the reaction product and optical purities of the ligand was observed for the reaction in CH2Cl2 whilst linear relationship for that in THF.

Original languageEnglish
Pages (from-to)8231-8232
Number of pages2
JournalTetrahedron Letters
Volume38
Issue number47
DOIs
Publication statusPublished - Nov 24 1997

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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