Stereodivergent Synthesis of α,α-Disubstituted α‑Amino Acids via Synergistic Cu/Ir Catalysis

Cu/Ir dual catalysis has been developed for the stereodivergent α-allylation of aldimine esters. The method enables the preparation of a series of nonproteinogenic α-amino acids (α-AAs) bearing two contiguous stereogenic centers in high yield with excellent stereoselectivity. All four product stereo...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2018-01, Vol.140 (4), p.1508-1513
Main Authors: Wei, Liang, Zhu, Qiao, Xu, Shi-Ming, Chang, Xin, Wang, Chun-Jiang
Format: Article
Language:English
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Summary:Cu/Ir dual catalysis has been developed for the stereodivergent α-allylation of aldimine esters. The method enables the preparation of a series of nonproteinogenic α-amino acids (α-AAs) bearing two contiguous stereogenic centers in high yield with excellent stereoselectivity. All four product stereoisomers could be obtained from the same set of starting materials via pairwise combination of two chiral catalysts. Notably, one-pot protocol could be successfully applied for the preparation of the bimetallic Cu/Ir complexes to simplify the manipulation of Cu/Ir dual catalysis. This method could be further utilized for the construction of the key intermediate of a bioactive pyrrolidine derivative and the concise synthesis of a plant growth regulator (2S,3S)-2-amino-3-cyclopropylbutanoic acid.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b12174