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Synthesis 2011(20): 3277-3286  
DOI: 10.1055/s-0030-1260201
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of Isoxazolinobenzoxepanes via Intramolecular Nitrile Oxide Cycloaddition

K. Ramachandiran, K. Karthikeyan, T. Nandhakumar, D. Muralidharan, P. T. Perumal*
Organic Chemistry Division, Central Leather Research Institute (CSIR), Adyar, Chennai 600020, Tamilnadu, India
Fax: +91(44)24911589; e-Mail: ptperumal@gmail.com;
Further Information

Publication History

Received 21 June 2011
Publication Date:
05 September 2011 (online)

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Abstract

Concise routes to the synthesis of indole-tethered nitrile oxides have been developed, and their intramolecular nitrile oxide cycloadditions were studied. Heterocyclic scaffolds involving isoxazolinobenzoxepane frameworks have been achieved via intramolecular nitrile oxide cycloaddition of 3-[1-(2-allyloxyphenyl)-2-nitroethyl]-1H-indole derivatives using (Boc)2O and DMAP. This protocol affords products with excellent trans-selectivity.

Key words

intramolecular nitrile oxide cycloaddition - Michael addition - isoxazolinobenzoxepanes - trans-selectivity

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Crystallographic data of compound 7e reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplemental publication No. CCDC-775950. 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 or email: deposit@ccdc.cam.ac.uk].