Ha, Min Woo Lee, Myungmo Choi, Sujee Kim, Seek Hong, Suckchang Park, Yohan Kim, Mi-hyun Kim, Taek-Soo Lee, Jihoon Lee, Jae Kyun Park, Hyeung-geun 2024-01-20T07:32:03Z 2024-01-20T07:32:03Z 2021-09-05 2015-03-20 0022-3263 https://pubs.kist.re.kr/handle/201004/125653 An efficient enantioselective synthetic method for alpha-amido-alpha-alkylmalonates via phase-transfer catalytic alpha-alkylation was successfully developed. The alpha-alkylation of alpha-amidomalonates under phase-transfer catalytic conditions (50% KOH, toluene, -40 degrees C) in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide afforded the corresponding alpha-amido-alpha-alkylmalonates in high chemical yields (up to 99%) and optical yields (up to 97% ee), which could be readily converted to versatile chiral intermediates bearing alpha-amino quaternary stereogenic centers. The synthetic potential of this methodology was demonstrated via the synthesis of chiral azlactone, oxazoline, and unnatural alpha-amino acid. English AMER CHEMICAL SOC BETA-KETO-ESTERS ASYMMETRIC-SYNTHESIS ELECTROPHILIC AMINATION KETOESTERS ACID HYDRAZINATION TRISOXAZOLINE Construction of Chiral alpha-Amino Quaternary Stereogenic Centers via Phase-Transfer Catalyzed Enantioselective alpha-Alkylation of alpha-Amidomalonates Article 10.1021/jo502791d 1 JOURNAL OF ORGANIC CHEMISTRY, v.80, no.6, pp.3270 - 3279 JOURNAL OF ORGANIC CHEMISTRY 80 6 3270 3279 scie scopus 000351558400035 2-s2.0-84925358844 Chemistry, Organic Chemistry Article BETA-KETO-ESTERS ASYMMETRIC-SYNTHESIS ELECTROPHILIC AMINATION KETOESTERS ACID HYDRAZINATION TRISOXAZOLINE α-amido-α-alkylmalonates phase-transfer catalytic α- alkylation X-ray crystallographic structure alkylating agents