Catalytic asymmetric allylations of achiral and chiral aldehydes via BINOL-Zr complex

Michio Kurosu, Miguel Lorca

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

The complex generated from BINOL, Zr(OtBu)4, and 4 Å MS in toluene-pivalonitrile is very effective for catalytic asymmetric allylation of aldehydes using allyltributyltin. The reactions of achiral aldehyde under these conditions are completed within 3 h using 10-20 mol% of the complex at -20°C. The ees of homoallylic alcohols can be enhanced up to 98% via the tandem asymmetric allylation-Oppenauer oxidations. The scope and limitations of these conditions for β-alkoxy aldehydes were extensively examined.

Original languageEnglish (US)
Pages (from-to)1765-1769
Number of pages5
JournalTetrahedron Letters
Volume43
Issue number10
DOIs
StatePublished - Mar 4 2002

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Allylation
Aldehydes
Toluene
Alcohols
Oxidation
naphthol BINOL

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Catalytic asymmetric allylations of achiral and chiral aldehydes via BINOL-Zr complex. / Kurosu, Michio; Lorca, Miguel.

In: Tetrahedron Letters, Vol. 43, No. 10, 04.03.2002, p. 1765-1769.

Research output: Contribution to journalArticle

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