Intramolecular Cycloaddition Reactions of Silyl Nitronate Tethered to Vinylsilyl Group: 2-Nitroalkanols as Precursors for Amino Polyols

Takayuki Kudoh, Teruhiko Ishikawa, Yoshihiro Shimizu, Seiki Saito

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

(Matrix presented) A method for converting 2-nitroalkanols to precursors for stereodefined amino polyols is described. Diphenylvinylsilylation of the 2-nitroalkanols' hydroxy groups and subsequent silyl nitronate generation by using TMS-CI and Et3N in CH3CN at 0°C to room temperature led to fused-bicyclic heterocycles through stereoselective intramolecular nitronate-olefin [3 + 2] cycloaddition reaction. Some examples for transforming the cycloadducts to amino polyols are also presented.

Original languageEnglish
Pages (from-to)3875-3878
Number of pages4
JournalOrganic Letters
Volume5
Issue number21
DOIs
Publication statusPublished - Oct 16 2003

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Cycloaddition
Cycloaddition Reaction
cycloaddition
alkenes
Alkenes
room temperature
matrices
Temperature
polyol

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Intramolecular Cycloaddition Reactions of Silyl Nitronate Tethered to Vinylsilyl Group : 2-Nitroalkanols as Precursors for Amino Polyols. / Kudoh, Takayuki; Ishikawa, Teruhiko; Shimizu, Yoshihiro; Saito, Seiki.

In: Organic Letters, Vol. 5, No. 21, 16.10.2003, p. 3875-3878.

Research output: Contribution to journalArticle

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