Polysubstituted Oxygen Heterocycles by a Reformatsky-Type Reaction/Reductive Cyclization Approach from Enantiopure β-Ketosulfoxides
The stereoselective synthesis of tetrasubstituted tetrahydrofurans and trisubstituted tetrahydropyrans bearing a sulfoxide was achieved by reductive cyclization (Et3SiH/TMSOTf) from the corresponding enantiopure hydroxy ketones protected as a dioxolane. These derivatives are easily accessible from a...
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| Veröffentlicht in: | Organic letters 2007-10, Vol.9 (22), p.4451-4454 |
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| container_title | Organic letters |
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| creator | Colobert, Françoise Choppin, Sabine Ferreiro-Mederos, Leticia Obringer, Michel Arratta, Sandra Luengo Urbano, Antonio Carreño, M. Carmen |
| description | The stereoselective synthesis of tetrasubstituted tetrahydrofurans and trisubstituted tetrahydropyrans bearing a sulfoxide was achieved by reductive cyclization (Et3SiH/TMSOTf) from the corresponding enantiopure hydroxy ketones protected as a dioxolane. These derivatives are easily accessible from a Reformatsky-type reaction between α-bromo-α‘-sulfinyl ketones and protected α- or β-ketoaldehydes, followed by diastereoselective reduction of the resulting β-ketosulfoxide. |
| doi_str_mv | 10.1021/ol701670g |
| format | Article |
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| ispartof | Organic letters, 2007-10, Vol.9 (22), p.4451-4454 |
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| language | eng |
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| title | Polysubstituted Oxygen Heterocycles by a Reformatsky-Type Reaction/Reductive Cyclization Approach from Enantiopure β-Ketosulfoxides |
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