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

Access to Document

Fingerprint Dive into the research topics of 'A novel intramolecular silyl nitronate cycloaddition route to dihydrofuraldehydes and dihydropyranaldehydes'. Together they form a unique fingerprint.

Cite this

@article{389b1efb14cf41e8883470d9715b40b7,

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)",

volume = "59",

pages = "3783--3785",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=0000436606&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000436606&partnerID=8YFLogxK

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 -