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Asymmetric intramolecular Diels-Alder reaction of a sulphoximine-substituted triene |
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| Authors: | Donald Craig |
| Institution: | Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, U.K. Rhône-Poulenc Agriculture Limited, Fyfield Road, Ongar, Essex CM5 OHW, U.K. |
| Abstract: | The synthesis and thermally-induced intramolecular Diels-Alder (IMDA) reaction of (S)s-(+)-S-(1E,7E)-1,7,9-decatrienyl]-S-phenyl-N-(p-tolylsulphonyl)sulphoximine 4 is described. A model is proposed for the cis-selectivity of the cycloaddition based on previous results from the reactions of sulphonyl-substituted trienes. The stereochemistry of the major cis-fused cycloadduct is determined by single-crystal X-ray analysis of that obtained from reaction of racemic 4. |
| Keywords: | Bicyclo[4 4 0]decene intramolecular Diels-Alder sulphoximine triene |
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