Synthesis of Tertiary α-Hydroxy Acids by Silylene Transfer to α-Keto Esters

2007-10-25T00:00:00Z (GMT) by Brett E. Howard K. A. Woerpel
α-Keto esters can be converted into α-hydroxy acids in a single flask involving metal-catalyzed silylene transfer, 6π-electrocyclization, Ireland−Claisen rearrangement, and hydrolysis. This reaction sequence is stereoselective and tolerates alkyl- and aryl-substituted α-keto ester substrates as well as an α-imino ester.