A new method for the preparation of silyl enol ethers from carbonyl compounds and (trimethylsilyl)diazomethane in a regiospecific and highly stereoselective manner |
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| Authors: | Aggarwal Varinder K Sheldon Chris G Macdonald Gregor J Martin William P |
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| Institution: | School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK. v.aggarwal@bristol.ac.uk |
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| Abstract: | The reaction of lithium (trimethylsilyl)diazomethane with aldehydes and ketones has been investigated, and it has been found that quenching at low temperature with MeOH followed by addition of Rh2(OAc)4 gave silyl enol ethers in high yields. Quenching with other electrophiles (e.g., deuterium, MeI) gave terminal and substituted silyl enol ethers with complete control over regio- and stereochemistry. The mechanism of this novel process has been mapped out through a combination of deuterium labeling, ReactIR, and isolation of reaction intermediates. |
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