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Lewis Acid Catalyzed Enlargement of Cyclic β-Alkoxyenals and One-Pot Synthesis of Polyfunctional Enoxysilanes Derived from Aucubin with Trimethylsilyldiazomethane
Pyrane to oxepane in one step: Highly regio‐ and stereoselective homologations dependent on the nature of carbonyl function and catalysts have been observed during the formation of enoxysilanes (see scheme). Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and AlCl3 were identified as suitable cata...
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| Published in: | Chemistry : a European journal 2013-04, Vol.19 (15), p.4686-4690 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c3838-48a041b45ee5b1fe6f38015141ef0c306baf2a6a4a1f2c6a633f1935dcb36c2f3 |
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| cites | cdi_FETCH-LOGICAL-c3838-48a041b45ee5b1fe6f38015141ef0c306baf2a6a4a1f2c6a633f1935dcb36c2f3 |
| container_end_page | 4690 |
| container_issue | 15 |
| container_start_page | 4686 |
| container_title | Chemistry : a European journal |
| container_volume | 19 |
| creator | Lemus, Christelle Poleschak, Marko Gailly, Sophie Desage-El Murr, Marine Koch, Michel Deguin, Brigitte |
| description | Pyrane to oxepane in one step: Highly regio‐ and stereoselective homologations dependent on the nature of carbonyl function and catalysts have been observed during the formation of enoxysilanes (see scheme). Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and AlCl3 were identified as suitable catalysts to promote the homologation and ring‐enlargement. |
| doi_str_mv | 10.1002/chem.201203968 |
| format | article |
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| fulltext | fulltext |
| identifier | ISSN: 0947-6539 |
| ispartof | Chemistry : a European journal, 2013-04, Vol.19 (15), p.4686-4690 |
| issn | 0947-6539 1521-3765 |
| language | eng |
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| source | Wiley |
| subjects | aldehydes Aldehydes - chemistry Catalysis Diazomethane - analogs & derivatives Diazomethane - chemical synthesis Diazomethane - chemistry enals homologation Hydrocarbons, Cyclic - chemistry Iridoid Glucosides - chemical synthesis Iridoid Glucosides - chemistry Lewis acids Lewis Acids - chemistry Molecular Structure Stereoisomerism Trimethylsilyl Compounds - chemical synthesis Trimethylsilyl Compounds - chemistry trimethylsilyldiazomethane |
| title | Lewis Acid Catalyzed Enlargement of Cyclic β-Alkoxyenals and One-Pot Synthesis of Polyfunctional Enoxysilanes Derived from Aucubin with Trimethylsilyldiazomethane |
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