Stereocontrolled preparation of 1,2-diol with quaternary chiral center

Yoshihisa Murata, Tomoyuki Kamino, Seijiro Hosokawa, Susumu Kobayashi

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Development of an enantio- and stereoselective construction of 1,2-diols including a quaternary chiral center was achieved by a titanium-mediated aldol reaction of lactates bearing chiral oxazolidine-2-ones. anti-Aldol and syn-aldol were selectively obtained by the choice of a benzyl and TBS protecting group, respectively. Plausible transition states are also shown based on the stereochemistry of the enolate anion.

Original languageEnglish
Pages (from-to)8121-8123
Number of pages3
JournalTetrahedron Letters
Issue number45
Publication statusPublished - 2002 Nov 4
Externally publishedYes


ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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