10.1021/ol702148x.s003
Brett E. Howard
Brett E.
Howard
K. A. Woerpel
K. A.
Woerpel
Synthesis of Tertiary α-Hydroxy Acids
by Silylene Transfer to α-Keto Esters
American Chemical Society
2007
esters
silylene
reaction sequence
Ireland
Ester
acid
stereoselective
imino
flask
transfer
electrocyclization
Keto
ester
Hydroxy
Silylene Transfer
keto
substrate
alkyl
hydroxy
hydrolysis
rearrangement
Synthesi
Acid
Tertiary
2007-10-25 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Tertiary_Hydroxy_Acids_by_Silylene_Transfer_to_Keto_Esters/2979211
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.