Enantioselective Synthesis of Chiral α‐Alkylthiomalonates via a Phase‐Transfer‐Catalyzed α‐Sulfenylation of α‐Alkylmalonates. Issue 9 (21st August 2019)

• Record Type: Journal Article
• Authors: Jung, So Hyun; Kim, Byungsoo; Park, Cheonhyoung; Kim, Jeongseok; Ha, Min Woo; Hong, Suckchang; Park, Hyeung‐geun
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 9(2019)
• Page Start: 1732
• Page End: 1739
• Publication Date: 2019-08-21
• Subjects: asymmetric synthesis -- enantioselectivity -- phase-transfer catalysis -- α-sulfenylation -- α-thiomalonates; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900346
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: A synthetic method for accessing chiral α‐alkylthio‐α‐alkylmalonates was successfully established. The enantioselective α‐sulfenylation of α‐alkylmalonates via phase‐transfer catalysis [ N ‐alkylthiophthalimide, 50% aq. KOH, toluene, −40 °C and N ‐2′, 3′, 4′‐trifluorophenyl‐dihydroquinidium bromide] provided the corresponding α‐alkylthio‐α‐alkylmalonates in high chemical yields (up to 97%) and optical purities (up to 90% ee ). Abstract : Phase‐transfer Catalysis : Diverse chiral α‐alkylthio‐α‐alkylmalonates were successfully synthesized via an enantioselective phase‐transfer catalytic α‐sulfenylation of α‐alkylmalonates in good yields and high optical purities using N‐alkylthiophthalimides in the presence of N‐2′, 3′, 4′‐trifluorophenyl‐dihydroquinidium bromide.