Enantioselective Synthesis of Chiral α-Alkylthiomalonates via a Phase-Transfer-Catalyzed α-Sulfenylation of α-Alkylmalonates

Jung, So Hyun; Kim, Byungsoo; Park, Cheonhyoung; Kim, Jeongseok; Ha, Min Woo; Hong, Suckchang; Park, Hyeung-geun

doi:10.1002/ajoc.201900346

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Enantioselective Synthesis of Chiral α-Alkylthiomalonates via a Phase-Transfer-Catalyzed α-Sulfenylation of α-Alkylmalonates : Enantioselective Synthesis of Chiral alpha-Alkylthiomalonates via a Phase-Transfer-Catalyzed alpha-Sulfenylation of alpha-Alkylmalonates

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Authors: Jung, So Hyun; Kim, Byungsoo; Park, Cheonhyoung; Kim, Jeongseok; Ha, Min Woo; Hong, Suckchang; Park, Hyeung-geun

Issue Date: 2019-09

Publisher: Wiley - VCH Verlag GmbH & Co. KG

Citation: Asian Journal of Organic Chemistry, Vol.8 No.9, pp.1732-1739

Abstract: A synthetic method for accessing chiral alpha-alkylthio-alpha-alkylmalonates was successfully established. The enantioselective alpha-sulfenylation of alpha-alkylmalonates via phase-transfer catalysis [N-alkylthiophthalimide, 50% aq. KOH, toluene, -40 degrees C and N-2 ',3 ',4 '-trifluorophenyl-dihydroquinidium bromide] provided the corresponding alpha-alkylthio-alpha-alkylmalonates in high chemical yields (up to 97%) and optical purities (up to 90% ee).