期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 18, 页码 8498-8505出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c02707
关键词
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资金
- JSPS KAKENHI [JP15H05846, JP18H04262, JP18H04263, JP17H03972, JP16K08166]
- Naito Foundation
- Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED [JP19am0101091]
- Qdai-jump Research Program
- Takeda Science Foundation
Unnatural alpha-amino acids are invaluable building blocks in synthetic organic chemistry and could upgrade the function of peptides. We developed a new mode for catalytic activation of amino acid Schiff bases, serving as a platform for highly congested unnatural alpha-amino acid synthesis. The redox active copper catalyst enabled efficient cross-coupling to construct contiguous tetrasubstituted carbon centers. The broad functional group compatibility highlights the mildness of the present catalysis. Notably, we achieved successive beta-functionalization and oxidation of amino acid Schiff bases to afford dehydroalanine derivatives bearing tetrasubstituted carbon. A three-component cross-coupling reaction of an amino acid Schiff base, alkyl bromides, and styrene derivatives demonstrated the high utility of the present method. The diastereoselective reaction was also achieved using menthol derivatives as a chiral auxiliary, delivering enantiomerically enriched alpha-amino acid bearing alpha,beta-continuous tetrasubstituted carbon. The synthesized highly congested unnatural alpha-amino acid could be derivatized and incorporated into peptide synthesis.
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