Stereoselective formation of functionalized 2-aryl-tetrahydrofurans from aromatic aldehydes via intramolecular 1,3-dipolar cycloadditions (inoc and iooc)

Alfred Hassner; K. M.Lokanatha Rai; Wim Dehaen

doi:10.1080/00397919408010169

Stereoselective formation of functionalized 2-aryl-tetrahydrofurans from aromatic aldehydes via intramolecular 1,3-dipolar cycloadditions (inoc and iooc)

Alfred Hassner, K. M.Lokanatha Rai, Wim Dehaen

Department of Chemistry

Bar-Ilan University

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

21 Scopus citations

Abstract

a-Allyloxyaldoximes 8, formed by the reduction of ß-nitrostyrenes 5 with SnCl2-2H20 in the presence of an unsaturated alcohol, undergo either thermally induced intramolecular oxime olefin cycloaddition (IOOC) to bicyclic isoxazolidines 7, with stereospecific introduction of three stereocenters, or nitrile oxide olefin cycloadditions (INOC) to bicyclic isoxazolines 6. This provides an entry into functionalized tetrahydrofurans and tetrahydropyrans.

Original language	English
Pages (from-to)	1669-1682
Number of pages	14
Journal	Synthetic Communications
Volume	24
Issue number	12
DOIs	https://doi.org/10.1080/00397919408010169
State	Published - 1 Jun 1994

Bibliographical note

Funding Information:
Acknowledgement: Support of this research by a grant from the US-Israel

Funding

Acknowledgement: Support of this research by a grant from the US-Israel

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US-Israel

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10.1080/00397919408010169

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title = "Stereoselective formation of functionalized 2-aryl-tetrahydrofurans from aromatic aldehydes via intramolecular 1,3-dipolar cycloadditions (inoc and iooc)",

abstract = "a-Allyloxyaldoximes 8, formed by the reduction of {\ss}-nitrostyrenes 5 with SnCl2-2H20 in the presence of an unsaturated alcohol, undergo either thermally induced intramolecular oxime olefin cycloaddition (IOOC) to bicyclic isoxazolidines 7, with stereospecific introduction of three stereocenters, or nitrile oxide olefin cycloadditions (INOC) to bicyclic isoxazolines 6. This provides an entry into functionalized tetrahydrofurans and tetrahydropyrans.",

author = "Alfred Hassner and Rai, \{K. M.Lokanatha\} and Wim Dehaen",

note = "Funding Information: Acknowledgement: Support of this research by a grant from the US-Israel",

year = "1994",

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doi = "10.1080/00397919408010169",

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T1 - Stereoselective formation of functionalized 2-aryl-tetrahydrofurans from aromatic aldehydes via intramolecular 1,3-dipolar cycloadditions (inoc and iooc)

AU - Hassner, Alfred

AU - Rai, K. M.Lokanatha

AU - Dehaen, Wim

N1 - Funding Information: Acknowledgement: Support of this research by a grant from the US-Israel

PY - 1994/6/1

Y1 - 1994/6/1

N2 - a-Allyloxyaldoximes 8, formed by the reduction of ß-nitrostyrenes 5 with SnCl2-2H20 in the presence of an unsaturated alcohol, undergo either thermally induced intramolecular oxime olefin cycloaddition (IOOC) to bicyclic isoxazolidines 7, with stereospecific introduction of three stereocenters, or nitrile oxide olefin cycloadditions (INOC) to bicyclic isoxazolines 6. This provides an entry into functionalized tetrahydrofurans and tetrahydropyrans.

AB - a-Allyloxyaldoximes 8, formed by the reduction of ß-nitrostyrenes 5 with SnCl2-2H20 in the presence of an unsaturated alcohol, undergo either thermally induced intramolecular oxime olefin cycloaddition (IOOC) to bicyclic isoxazolidines 7, with stereospecific introduction of three stereocenters, or nitrile oxide olefin cycloadditions (INOC) to bicyclic isoxazolines 6. This provides an entry into functionalized tetrahydrofurans and tetrahydropyrans.

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ER -

Stereoselective formation of functionalized 2-aryl-tetrahydrofurans from aromatic aldehydes via intramolecular 1,3-dipolar cycloadditions (inoc and iooc)

Abstract

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