Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene-tethered nitrile oxides

Ming Chang P. Yeh; Chi Fen Jou; Wei Tzou Yeh; Da Yu Chiu; N. Ravi Kumar Reddy

doi:10.1016/j.tet.2004.10.078

Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene-tethered nitrile oxides

Ming Chang P. Yeh, Chi Fen Jou, Wei Tzou Yeh, Da Yu Chiu, N. Ravi Kumar Reddy

Department of Chemistry

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

21 Citations (Scopus)

Abstract

Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene- and -1,3,5-triene-tethered nitrile oxides gave tricyclic isoxazolines as a single stereoisomer in most cases. The relative stereochemistry of tricycle-fused isoxazolines resulting from 1,3-dipolar cycloaddition of cyclo-1,3-diene- tethered nitrile oxides is cis-cis, whereas from cyclohepta-1,3,5-triene- tethered nitrile oxides the cis-trans isomer predominates.

Original language	English
Pages (from-to)	493-500
Number of pages	8
Journal	Tetrahedron
Volume	61
Issue number	2
DOIs	https://doi.org/10.1016/j.tet.2004.10.078
Publication status	Published - 2005 Jan 10

Keywords

Aldoximes
Cyclohepta-1,3,5-trienes
Cyclohexa- and cyclohepta-1,3-dienes
Isoxazolines

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2004.10.078

Cite this

@article{bafdccf4d286408e9167b5f3fdeccae2,

title = "Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene-tethered nitrile oxides",

abstract = "Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene- and -1,3,5-triene-tethered nitrile oxides gave tricyclic isoxazolines as a single stereoisomer in most cases. The relative stereochemistry of tricycle-fused isoxazolines resulting from 1,3-dipolar cycloaddition of cyclo-1,3-diene- tethered nitrile oxides is cis-cis, whereas from cyclohepta-1,3,5-triene- tethered nitrile oxides the cis-trans isomer predominates.",

keywords = "Aldoximes, Cyclohepta-1,3,5-trienes, Cyclohexa- and cyclohepta-1,3-dienes, Isoxazolines",

author = "Yeh, {Ming Chang P.} and Jou, {Chi Fen} and Yeh, {Wei Tzou} and Chiu, {Da Yu} and Reddy, {N. Ravi Kumar}",

note = "Funding Information: This work was supported by grants from National Taiwan Normal University (ORD 92-2) and National Science Council (NSC 92-2113-M-003-009). ",

year = "2005",

month = jan,

day = "10",

doi = "10.1016/j.tet.2004.10.078",

language = "English",

volume = "61",

pages = "493--500",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

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T1 - Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene-tethered nitrile oxides

AU - Yeh, Ming Chang P.

AU - Jou, Chi Fen

AU - Yeh, Wei Tzou

AU - Chiu, Da Yu

AU - Reddy, N. Ravi Kumar

N1 - Funding Information: This work was supported by grants from National Taiwan Normal University (ORD 92-2) and National Science Council (NSC 92-2113-M-003-009).

PY - 2005/1/10

Y1 - 2005/1/10

N2 - Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene- and -1,3,5-triene-tethered nitrile oxides gave tricyclic isoxazolines as a single stereoisomer in most cases. The relative stereochemistry of tricycle-fused isoxazolines resulting from 1,3-dipolar cycloaddition of cyclo-1,3-diene- tethered nitrile oxides is cis-cis, whereas from cyclohepta-1,3,5-triene- tethered nitrile oxides the cis-trans isomer predominates.

AB - Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene- and -1,3,5-triene-tethered nitrile oxides gave tricyclic isoxazolines as a single stereoisomer in most cases. The relative stereochemistry of tricycle-fused isoxazolines resulting from 1,3-dipolar cycloaddition of cyclo-1,3-diene- tethered nitrile oxides is cis-cis, whereas from cyclohepta-1,3,5-triene- tethered nitrile oxides the cis-trans isomer predominates.

KW - Aldoximes

KW - Cyclohepta-1,3,5-trienes

KW - Cyclohexa- and cyclohepta-1,3-dienes

KW - Isoxazolines

UR - http://www.scopus.com/inward/record.url?scp=9744222886&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=9744222886&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2004.10.078

DO - 10.1016/j.tet.2004.10.078

M3 - Article

AN - SCOPUS:9744222886

SN - 0040-4020

VL - 61

SP - 493

EP - 500

JO - Tetrahedron

JF - Tetrahedron

IS - 2

ER -

Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene-tethered nitrile oxides

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 248698: Experimental Crystal Structure Determination

CCDC 248699: Experimental Crystal Structure Determination

CCDC 248701: Experimental Crystal Structure Determination

Cite this

Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene-tethered nitrile oxides

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 248698: Experimental Crystal Structure Determination

CCDC 248699: Experimental Crystal Structure Determination

CCDC 248701: Experimental Crystal Structure Determination

Cite this