Hydrogen-Bond-Assisted Sequential Reaction of Silyl Glyoxylates: Stereoselective Synthesis of Silyl Enol Ethers
| Autor: | Pinhua Li, Lei Wang, Chen Zhu, Man-Yi Han, Xiu-Xia Liang, Bin Guan |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Nitroaldol reaction
Silylation 010405 organic chemistry Hydrogen bond Organic Chemistry High selectivity Brook rearrangement 010402 general chemistry 01 natural sciences Biochemistry Enol Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Glyoxylates Stereoselectivity Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 23:54-59 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.0c03683 |
| Popis: | A novel hydrogen-bond-assisted sequential reaction of silyl glyoxylates is described. This method provides an efficient strategy for the synthesis of silyl enol ethers with high selectivity. In these transformations, hydrogen bonds from 2-nitroethanol and its derivatives are critical to the stereochemical outcome. Both E- and Z-isomers are achieved via Henry reaction/Brook rearrangement/elimination and Henry reaction/Brook rearrangement/retro-Henry reaction/elimination processes, respectively (up to 99:1 Z-selectivity, and 9.2:1 E-selectivity). |
| Databáze: | OpenAIRE |
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