Reductive Fragmentation of Tetrazoles: Mechanistic Insights and Applications toward the Stereocontrolled Synthesis of 2,6-Polysubstituted Morpholines
A new methodology to synthesize 2,6-di-, and 2,2′,6-trisubstituted morpholines via the reduction of oxabicyclic tetrazoles under mild conditions is described. The reaction proved successful for a wide range of tetrazoles, including sterically encumbered ones harboring gem-substituents on tertiary ca...
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| Veröffentlicht in: | Organic letters 2019-09, Vol.21 (17), p.6593-6596 |
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| container_issue | 17 |
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| container_title | Organic letters |
| container_volume | 21 |
| creator | Duchamp, Edouard Simard, Benoit Deschênes Hanessian, Stephen |
| description | A new methodology to synthesize 2,6-di-, and 2,2′,6-trisubstituted morpholines via the reduction of oxabicyclic tetrazoles under mild conditions is described. The reaction proved successful for a wide range of tetrazoles, including sterically encumbered ones harboring gem-substituents on tertiary carbon centers. The mechanism for the decades-old reduction of tetrazoles to secondary amines is elucidated. |
| doi_str_mv | 10.1021/acs.orglett.9b01842 |
| format | Article |
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| language | eng |
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| source | ACS Publications |
| title | Reductive Fragmentation of Tetrazoles: Mechanistic Insights and Applications toward the Stereocontrolled Synthesis of 2,6-Polysubstituted Morpholines |
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