Synthesis of tertiary alpha-hydroxy acids by silylene transfer to alpha-keto esters |
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| Authors: | Howard Brett E Woerpel K A |
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| Affiliation: | Department of Chemistry, University of California, Irvine, California 92697-2025, USA. |
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| Abstract: | Alpha-keto esters can be converted into alpha-hydroxy acids in a single flask involving metal-catalyzed silylene transfer, 6pi-electrocyclization, Ireland-Claisen rearrangement, and hydrolysis. This reaction sequence is stereoselective and tolerates alkyl- and aryl-substituted alpha-keto ester substrates as well as an alpha-imino ester. |
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