A novel intramolecular silyl nitronate cycloaddition route to dihydrofuraldehydes and dihydropyranaldehydes

Jetty L. Duffy; Mark J. Kurth

A novel intramolecular silyl nitronate cycloaddition route to dihydrofuraldehydes and dihydropyranaldehydes

Jetty L. Duffy, Mark J. Kurth

Chemistry

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

The novel transformation (1 → 3) of propargylic or homopropargylic nitroethers to dihydrofuraldehydes (n = 0) or dihydropyranaldehydes (n = 1) is reported. The transformation proceeds by a silyl nitronate olefin cycloaddition to an N-[(trimethylsilyl)oxy]isoxazolidine intermediate which, upon acid workup, undergoes desilylation with subsequent elimination of hyponitrous acid to 3.

Original language	English (US)
Pages (from-to)	3783-3785
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	59
Issue number	14
State	Published - 1994

ASJC Scopus subject areas

Organic Chemistry

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title = "A novel intramolecular silyl nitronate cycloaddition route to dihydrofuraldehydes and dihydropyranaldehydes",

abstract = "The novel transformation (1 → 3) of propargylic or homopropargylic nitroethers to dihydrofuraldehydes (n = 0) or dihydropyranaldehydes (n = 1) is reported. The transformation proceeds by a silyl nitronate olefin cycloaddition to an N-[(trimethylsilyl)oxy]isoxazolidine intermediate which, upon acid workup, undergoes desilylation with subsequent elimination of hyponitrous acid to 3.",

author = "Duffy, {Jetty L.} and Kurth, {Mark J.}",

year = "1994",

language = "English (US)",

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journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - A novel intramolecular silyl nitronate cycloaddition route to dihydrofuraldehydes and dihydropyranaldehydes

AU - Duffy, Jetty L.

AU - Kurth, Mark J.

PY - 1994

Y1 - 1994

N2 - The novel transformation (1 → 3) of propargylic or homopropargylic nitroethers to dihydrofuraldehydes (n = 0) or dihydropyranaldehydes (n = 1) is reported. The transformation proceeds by a silyl nitronate olefin cycloaddition to an N-[(trimethylsilyl)oxy]isoxazolidine intermediate which, upon acid workup, undergoes desilylation with subsequent elimination of hyponitrous acid to 3.

AB - The novel transformation (1 → 3) of propargylic or homopropargylic nitroethers to dihydrofuraldehydes (n = 0) or dihydropyranaldehydes (n = 1) is reported. The transformation proceeds by a silyl nitronate olefin cycloaddition to an N-[(trimethylsilyl)oxy]isoxazolidine intermediate which, upon acid workup, undergoes desilylation with subsequent elimination of hyponitrous acid to 3.

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M3 - Article

AN - SCOPUS:0000436606

VL - 59

SP - 3783

EP - 3785

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 14

ER -

A novel intramolecular silyl nitronate cycloaddition route to dihydrofuraldehydes and dihydropyranaldehydes

Abstract

ASJC Scopus subject areas

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