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Carboxylate-Directed Pd-Catalyzed β-C(sp<SUP>3</SUP>)-H Arylation of <i>N</i>-Methyl Alanine Derivatives for Diversification of Bioactive Peptides
- Yeom, Suyeon;
- Kim, Do Young;
- Kim, Seungwoo;
- Gontala, Arjun;
- Park, Jimin;
- ... Kim, Hak Joong;
- 외 1명
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4초록
This study presents a Pd(II)-catalyzed method for the beta-C(sp(3))-H arylation of N-Cbz- or N-Fmoc-protected N-methyl alanines, providing ready access to building blocks for N-methylated peptide synthesis. For this transformation, the native carboxylate was exploited as the directing group, attributing its success to the use of a monoprotected amino-pyridine ligand. Its synthetic utility was demonstrated by facile generation of nine analogues of the naturally occurring N-methylated cyclic peptide cycloaspeptide A.
키워드
C-H FUNCTIONALIZATION; AMINO-ACIDS; C(SP(3))-H ARYLATION; BOND FUNCTIONALIZATION; CYCLIC PENTAPEPTIDES; COUPLING REACTIONS; LIGAND
- 제목
- Carboxylate-Directed Pd-Catalyzed β-C(sp<SUP>3</SUP>)-H Arylation of <i>N</i>-Methyl Alanine Derivatives for Diversification of Bioactive Peptides
- 저자
- Yeom, Suyeon; Kim, Do Young; Kim, Seungwoo; Gontala, Arjun; Park, Jimin; Lee, Yong Ho; Kim, Hak Joong
- 발행일
- 2023-12-12
- 유형
- Article
- 저널명
- Organic Letters
- 권
- 25
- 호
- 50
- 페이지
- 9008 ~ 9013