Synthesis of tertiary alpha-hydroxy acids by silylene transfer to alpha-keto esters.
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.
Howard
Brett E
BE
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Woerpel
K A
KA
D004952:Esters / Q000737:chemistry; D006880:Hydroxy Acids / Q000138:chemical synthesis*; D015394:Molecular Structure
D004952:Esters; D006880:Hydroxy Acids