Reversal of stereoselectivity in [5 + 2] pyrone--alkene cycloadditons using a sulfoxide-to-sulfoximine switch. Enantiodivergent synthesis of 8-oxabicyclo[3.2.1]octane systems |
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Authors: | López F Castedo L Mascareñas J L |
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Institution: | Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, 15706 Santiago de Compostela, Spain. |
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Abstract: | reaction: see text] Switching from a sulfinyl to a sulfonimidoyl group allows the reversal of the sense of asymmetric induction in thermal 5C + 2C] intramolecular pyrone-alkene cycloadditions. Removal of the sulfoximine unit from the resulting cycloadducts yields optically active oxabicyclic systems that are enantiomeric to those obtained using the sulfinyl chiral auxiliary. |
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