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

Article abstract of DOI:10.1080/00397919408010169

α-Allyloxyaldoximes 8, formed by the reduction of β-nitrostyrenes 5 with SnCl₂-2H₂O 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.

Full text of DOI:10.1080/00397919408010169

This article was downloaded by: [McMaster University]
On: 10 December 2014, At: 09:53
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH,
UK
Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
Stereoselective Formation
of Functionalized 2-Aryl-
tetrahydrofurans from
Aromatic Aldehydes via
Intramolecular 1,3-Dipolar
Cycloadditions (INOC and IOOC)
Alfred Hassner a , K. M. Lokanatha Rai a & Wim
Dehaen a
a Department of Chemistry , Bar-Ilan University ,
Ramat Gan, 52900, Israel
Published online: 23 Sep 2006.
To cite this article: Alfred Hassner , K. M. Lokanatha Rai & Wim Dehaen (1994)
Stereoselective Formation of Functionalized 2-Aryl-tetrahydrofurans from Aromatic
Aldehydes via Intramolecular 1,3-Dipolar Cycloadditions (INOC and IOOC), Synthetic
Communications: An International Journal for Rapid Communication of Synthetic
Organic Chemistry, 24:12, 1669-1682, DOI: 10.1080/00397919408010169
To link to this article: http://dx.doi.org/10.1080/00397919408010169
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the
information (the “Content”) contained in the publications on our platform.
However, Taylor & Francis, our agents, and our licensors make no

representations or warranties whatsoever as to the accuracy, completeness,
or suitability for any purpose of the Content. Any opinions and views
expressed in this publication are the opinions and views of the authors, and
are not the views of or endorsed by Taylor & Francis. The accuracy of the
Content should not be relied upon and should be independently verified with
primary sources of information. Taylor and Francis shall not be liable for any
losses, actions, claims, proceedings, demands, costs, expenses, damages,
and other liabilities whatsoever or howsoever caused arising directly or
indirectly in connection with, in relation to or arising out of the use of the
Content.
This article may be used for research, teaching, and private study purposes.
Any substantial or systematic reproduction, redistribution, reselling, loan,
sub-licensing, systematic supply, or distribution in any form to anyone is
expressly forbidden. Terms & Conditions of access and use can be found at
http://www.tandfonline.com/page/terms-and-conditions