A practical four-step sequence for the synthesis of alpha,delta-dioxoesters with high enantiomeric excess was developed. It makes use of a regio- and stereoselective Michael addition of a chiral ketimine to ethyl 2-(phenylthio)-2-propenoate as a key transformation. The synthetic elaboration of the Michael adduct provides the new ethyl 3-(1-methyl-2-oxo-cyclohexyl)-2-oxopropanoate, bearing a quaternary stereocenter with 95% ee and high yield.
Synthesis of Ethyl (S)-3-(1-Methyl-2-Oxo-Cyclohexyl)-2-Oxopropanoate Through Stereoselective Michael Addition / D.C.M. Albanese, N. Gaggero. - In: MOLBANK. - ISSN 1422-8599. - 2025:3(2025 Aug 28), pp. M2055.1-M2055.6. [10.3390/M2055]
Synthesis of Ethyl (S)-3-(1-Methyl-2-Oxo-Cyclohexyl)-2-Oxopropanoate Through Stereoselective Michael Addition
D.C.M. Albanese
Primo
;N. GaggeroUltimo
2025
Abstract
A practical four-step sequence for the synthesis of alpha,delta-dioxoesters with high enantiomeric excess was developed. It makes use of a regio- and stereoselective Michael addition of a chiral ketimine to ethyl 2-(phenylthio)-2-propenoate as a key transformation. The synthetic elaboration of the Michael adduct provides the new ethyl 3-(1-methyl-2-oxo-cyclohexyl)-2-oxopropanoate, bearing a quaternary stereocenter with 95% ee and high yield.
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