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Synthesis 2012(5): 755-766  
DOI: 10.1055/s-0031-1289707
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Intramolecular 1,3-Dipolar Nitrile Oxide Cycloaddition Using Baylis-Hillman Derivatives: Stereoselective Synthesis of Tricyclic Chromenoisoxazolines

Manickam Bakthadoss*, Jayakumar Srinivasan, Raman Selvakumar
Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Fax: +91(44)22352494; e-Mail: bhakthadoss@yahoo.com;
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Publication History

Received 20 October 2011
Publication Date:
13 February 2012 (online)

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Abstract

A novel protocol for the construction of tricyclic chromenoisoxazoline frameworks via an intramolecular 1,3-dipolar nitrile oxide cycloaddition (INOC) reaction using Baylis-Hillman derivatives is described for the first time. The INOC reaction leads to a novel class of angularly substituted fused tricyclic chromenoisoxazolines, with the creation of two rings and two adjacent stereocenters, one of them being an all-carbon quaternary center, in a unique fashion. The tricyclic chromenoisoxazolines are obtained in a highly stereoselective fashion with good yields.

Key words

1,3-dipolar nitrile oxide cycloaddition - chromenoisoxazolines - stereoselective synthesis - tricyclic framework

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16

The structures of compounds 5a and 9d were confirmed by single-crystal X-ray data. These data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 791956 (5a) and 791957 (9d). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk] or via www.ccdc.cam.ac.uk/data_request/cif.