Rh(II)/Mg(OtBu)2-Catalyzed Tandem One-Pot Synthesis of 1,4-Oxazepines and 1,4-Oxazines from N-Sulfonyl-1,2,3-triazoles and Glycidols
| Autor: | Sang‐gi Lee, U. Bin Kim, Da Jung Jung, Young Ok Ko, Hyun Ji Jeon |
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| Rok vydání: | 2016 |
| Předmět: |
Sulfonyl
chemistry.chemical_classification 010405 organic chemistry Stereochemistry Organic Chemistry One-pot synthesis Epoxide Regioselectivity 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Intramolecular force Oxazepine Lewis acids and bases Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 18:6432-6435 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.6b03328 |
| Popis: | A novel, one-pot route for the synthesis of nonaromatic ring-fused 1,4-oxazepines and 1,4-oxazines has been developed. The reaction features a sequential rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with glycidols, followed by a regioselective Lewis acid Mg(OtBu)2-catalyzed intramolecular ring-opening reaction. It has been found that the regioselectivity in the epoxide ring-opening was largely determined by the substituents on the glycidols. Thus, substituted glycidols (R2 ≠ H) afforded seven-membered oxazepine derivatives selectively, while unsubstituted glycidols (R2 = H) afforded six-membered oxazine derivatives. Plausible reaction pathways are elucidated and supported by experiments with several glycidols bearing different substituents around the epoxide functionality. |
| Databáze: | OpenAIRE |
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