1,3-Rearrangement of ketene-N,O-acetals

Tatsuo Suzuki, Masaharu Inui, Seijiro Hosokawa, Susumu Kobayashi

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Ketene N,O-acetals were prepared stereoselectively and submitted to a Lewis acid-mediated 1,3-rearrangement to afford C-alkylated products. The reactions proceeded in a stereoselective manner to construct a chiral quaternary carbon in high selectivity. The stereochemistry of the quaternary center was found to be opposite to that obtained by an anionic direct dienolate alkylation.

Original languageEnglish
Pages (from-to)3713-3716
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number18
DOIs
Publication statusPublished - 2003 Apr 28
Externally publishedYes

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Lewis Acids
Acetals
Stereochemistry
Alkylation
Carbon
ketene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

1,3-Rearrangement of ketene-N,O-acetals. / Suzuki, Tatsuo; Inui, Masaharu; Hosokawa, Seijiro; Kobayashi, Susumu.

In: Tetrahedron Letters, Vol. 44, No. 18, 28.04.2003, p. 3713-3716.

Research output: Contribution to journalArticle

Suzuki, T, Inui, M, Hosokawa, S & Kobayashi, S 2003, '1,3-Rearrangement of ketene-N,O-acetals', Tetrahedron Letters, vol. 44, no. 18, pp. 3713-3716. https://doi.org/10.1016/S0040-4039(03)00610-5
Suzuki, Tatsuo ; Inui, Masaharu ; Hosokawa, Seijiro ; Kobayashi, Susumu. / 1,3-Rearrangement of ketene-N,O-acetals. In: Tetrahedron Letters. 2003 ; Vol. 44, No. 18. pp. 3713-3716.
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