• Title/Summary/Keyword: ${\beta}$-Aminoalcohol

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Chiral 2-Amino Alcohol Derivatives Catalyze the Enantioselective α-Chlorination of β-Ketoesters

  • Zhang, Baohua;Guo, Ruixia;Liu, Sijie;Shi, Lanxiang;Li, Xiaoyun
    • Bulletin of the Korean Chemical Society
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    • v.35 no.6
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    • pp.1759-1762
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    • 2014

  • The enantioselective ${\alpha}$-chlorination of cyclic ${\beta}$-ketoesters catalyzed by chiral 2-aminoalcohol derivatives (2f) has been developed. For the optically active ${\alpha}$-chlorinated products, the isolated yields are in the range of 85-94% and the enantiomeric excesses are up to 84% ee.

  • https://doi.org/10.5012/bkcs.2014.35.6.1759 인용 PDF KSCI KPUBS HTML

Ring Opening of Pyrolidine and Formation of N-Protected Amino Ketones; Synthesis of 5-Amino-2-pentanone Derivatives (피롤리딘의 개환과 N-프로텍티드 아미노 케톤의 형성; 5-아미노-2-펜타논 유도체의 합성)

  • Park, Myung-Sook
    • YAKHAK HOEJI
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    • v.40 no.3
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    • pp.300-305
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    • 1996

  • The base-induced elimination of N-protected 2-(bromomethyl)pyrrolidines 12a-c with KHMDS in THF at -78$^{\circ}C$ for 1h gave exocyclic enamines 13a-c. The acidic catalyzed pr otonation on ${\beta}$-carbon atom of 2-(methylene)pyrrolidines 13a-c with $H_3PO_4$ formed endocyclic N-iminium intermediates 14(or 15). Nucleophilic attack of alpha-carbon atom and hydrolysis of N-iminium ion gave carbocationic adduct (aminoalcohol) 16 from which 5-amino-2-pentanones 17a-c were formed after deprotonation.

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