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

doi:10.1021/ol035423v

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 journal › Article › peer-review

25 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 language	English
Pages (from-to)	3875-3878
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	21
DOIs	https://doi.org/10.1021/ol035423v
Publication status	Published - Oct 16 2003

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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AU - Kudoh, Takayuki

AU - Ishikawa, Teruhiko

AU - Shimizu, Yoshihiro

AU - Saito, Seiki

PY - 2003/10/16

Y1 - 2003/10/16

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AB - (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.

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

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