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Highly Enantioselective Synthesis of γ-Carboxy-β-amino Acids via Desymmetric Alcoholysis of 3-Aminoglutaric Anhydrides
- Yang, Sehun;
- Lee, Jaeyong;
- Kim, Hong Ki;
- Lee, Geumwoo;
- Ha, Min Woo;
- ... Kim, Mi-hyun;
- 외 2명
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2초록
A highly enantioselective synthetic method of gamma-carboxy-beta-amino acids has been developed via the desymmetric alcoholysis of 3-aminoglutaric anhydrides. The asymmetric desymmetrization of N-trifluoroacetyl-N-acyl-3-aminoglutaric anhydrides with alcohols in the presence of bis-quinine-squaramide as a bifunctional organocatalyst afforded gamma-carboxy-beta-amino acids with up to 99% yield and 98% ee. These versatile compounds can be readily converted into various chiral derivatives. The practicality of this method was further demonstrated by its successful application in the synthesis of beta-amino acid and beta-amino lactone derivatives.
키워드
CATALYTIC ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; METHANOLYTIC DESYMMETRIZATION; STEREOSELECTIVE-SYNTHESIS; CYCLIC ANHYDRIDES; MANNICH REACTIONS; ALPHA-AMINO; DERIVATIVES; HYDROGENATION; PEPTIDES
- 제목
- Highly Enantioselective Synthesis of γ-Carboxy-β-amino Acids via Desymmetric Alcoholysis of 3-Aminoglutaric Anhydrides
- 저자
- Yang, Sehun; Lee, Jaeyong; Kim, Hong Ki; Lee, Geumwoo; Ha, Min Woo; Pavankumar, Kondapalli; Kim, Mi-hyun; Park, Hyeung-geun
- 발행일
- 2025-04
- 유형
- Article; Early Access
- 저널명
- Organic Letters
- 권
- 27
- 호
- 15
- 페이지
- 3988 ~ 3993