Asymmetric synthesis of chiral diols by the catalytic enantioselective dialkylation of tere-, iso-, and phthalaldehydes and by a catalytic enantioselective autoinductive reaction

Kenso Soai, Yukikazu Inoue, Tomohide Takahashi, Takanori Shibata

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33 Citations (Scopus)

Abstract

Optically pure aromatic diols were synthesized by the highly enantioselective dialkylation of aromatic dialdehydes with dialkylzincs in the presence of a catalytic amount of chiral aminoalcohol 1 or chiral thiophosphoramide alcohol 2 with Ti(0-i-Pr)4. The chiral titanium(IV) alkoxide of 4b, a diisopropylated product of isophthalaldehyde, catalyzed the addition of diisopropylzinc to isophthalaldehyde to gave a chiral zinc alkoxide of 4b with the same configuration by an enantioselective autoinductive reaction (up to 44% e.e.).

Original languageEnglish
Pages (from-to)13355-13362
Number of pages8
JournalTetrahedron
Volume52
Issue number42
DOIs
Publication statusPublished - 1996 Oct 14
Externally publishedYes

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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