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

Hiroki Mandai, Kosuke Ashihara, Koichi Mitsudo, Seiji Suga

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

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

Keywords

  • 1 3-Diol
  • Chiral DMAP derivative
  • Desymmetrization

ASJC Scopus subject areas

  • Chemistry(all)

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