N-Aryl Atropisomerism Induces Facial Selectivity in Benzonitrile Oxide Cycloadditions with Exocyclic Methylene Benzosultams
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 66(8) 874-881 https://doi.org/10.1071/CH13270
Submitted: 28 May 2013 Accepted: 27 June 2013 Published: 19 July 2013
Abstract
N-aryl methylene benzo-fused sultams (2,3-dihydrobenzo[d]isothiazole 1,1-dioxides) underwent [3+2] cycloaddition with benzonitrile oxide to give 5-spiro isoxazoline adducts with complete regioselectivity. Steric hindrance by atropisomerism around the N-aryl bond induced facial selectivity in these cycloadditions.
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