Direct enantioselective approach to oxazolo[4,5-e]isoindoles from [(S)R]-1-aminosubstituted-4-(p-tolylsulfinyl)-1,3-butadienes |
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| Affiliation: | 1. Department of Emergency Medicine, Yale School of Medicine, 464 Congress Avenue Suite 260, New Haven, CT 06519, United States of America;2. Department of Psychiatry, Yale School of Medicine, 34 Park Street, New Haven, CT 06519, United States of America |
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| Abstract: | The enantioselective construction of [3aS,5aR,8aR,8bR]-1-(p-methoxyphenyl)-3a,7-dimethyl-3a,5a,8b,8a-tetrahydro-1H-oxazolo[4,5-e]isoindole-2,6,8-trione is achieved from enantiopure [(S)R]-(1E,3E)-2-methyl-1-(p-methoxyphenyl)amino-4-(p-tolylsulfinyl)-1,3-butadiene and N-methylmaleimide through a short sequence involving a Diels–Alder reaction, a sulfoxide–sulfenate rearrangement and intramolecular cyclization. |
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