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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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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