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