Construction of Chiral alpha-Amino Quaternary Stereogenic Centers via Phase-Transfer Catalyzed Enantioselective alpha-Alkylation of alpha-Amidomalonates
- Authors
- 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
- Issue Date
- 20-Mar-2015
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.80, no.6, pp.3270 - 3279
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 80
- Number
- 6
- Start Page
- 3270
- End Page
- 3279
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/10695
- DOI
- 10.1021/jo502791d
- ISSN
- 0022-3263
- Abstract
- 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.
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Collections - 약학대학 > 약학과 > 1. Journal Articles
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