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

Yoshihisa Murata, Tomoyuki Kamino, Seijiro Hosokawa, Susumu Kobayashi

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

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
Volume43
Issue number45
DOIs
Publication statusPublished - 2002 Nov 4
Externally publishedYes

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Lactates
Bearings (structural)
Stereochemistry
Titanium
Anions
3-hydroxybutanal
oxazolidine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereocontrolled preparation of 1,2-diol with quaternary chiral center. / Murata, Yoshihisa; Kamino, Tomoyuki; Hosokawa, Seijiro; Kobayashi, Susumu.

In: Tetrahedron Letters, Vol. 43, No. 45, 04.11.2002, p. 8121-8123.

Research output: Contribution to journalArticle

Murata, Yoshihisa ; Kamino, Tomoyuki ; Hosokawa, Seijiro ; Kobayashi, Susumu. / Stereocontrolled preparation of 1,2-diol with quaternary chiral center. In: Tetrahedron Letters. 2002 ; Vol. 43, No. 45. pp. 8121-8123.
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