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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Benzonitrile Oxide Cycloadditions with Exocyclic Methylene Benzothiazepine Dioxides

Sarah J. Ryan A , Craig L. Francis A and G. Paul Savage A B
+ Author Affiliations
- Author Affiliations

A CSIRO Materials Science and Engineering, Private Bag 10, Clayton South MDC, Vic. 3169, Australia.

B Corresponding author. Email: paul.savage@csiro.au

Australian Journal of Chemistry 67(3) 381-388 https://doi.org/10.1071/CH13444
Submitted: 26 August 2013  Accepted: 23 September 2013   Published: 14 October 2013

Abstract

N-substituted 5-methylene-2,3,4,5-tetrahydrobenzo[f][1,2]thiazepine 1,1-dioxides underwent 1,3-dipolar cycloaddition with benzonitrile oxide, generated in situ, to give isoxazoline spiro adducts. The cycloadditions were completely regioselective to give the hitherto unreported 3,4-dihydro-2H,4′H-spiro[benzo[f][1,2]thiazepine-5,5′-isoxazole] 1,1-dioxide cycloadduct. Where the N-substituent on the sulfonamide cycloaddition precursor was a 2-substituted arene, the resulting atropisomerism along the N-aryl bond led to facial selectivity in the cycloaddition reaction, with greater than 90 % diastereoselectivity.


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