Enantioselective Desymmetrization of 1,3-Diols by a Chiral DMAP Derivative

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Abstract

We developed an enantioselective desymmetrization of 1,3-diols by a chiral N,N-dimethyl-4-aminopyridine (DMAP) derivative containing a 1,1-binaphthyl with tert-alcohol units. The reactions required only 0.1 mol% of catalyst and showed moderate to high chemoselectivity (monoacylation vs. diacylation) and enantioselectivity (14 examples, up to 95:5 er). Several control experiments revealed that diol units in both the substrate and the catalyst are important to achieve high enantioselectivity.

Original languageEnglish
Pages (from-to)1360-1363
Number of pages4
JournalChemistry Letters
Volume47
Issue number11
DOIs
Publication statusPublished - Jan 1 2018

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4-Aminopyridine
Enantioselectivity
Derivatives
Catalysts
Alcohols
Substrates
Experiments

Keywords

  • 1 3-Diol
  • Chiral DMAP derivative
  • Desymmetrization

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Enantioselective Desymmetrization of 1,3-Diols by a Chiral DMAP Derivative. / Mandai, Hiroki; Ashihara, Kosuke; Mitsudo, Koichi; Suga, Seiji.

In: Chemistry Letters, Vol. 47, No. 11, 01.01.2018, p. 1360-1363.

Research output: Contribution to journalArticle

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