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Synfacts 2017; 13(11): 1176
DOI: 10.1055/s-0036-1591335
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Chiral γ-Phosphono-α-Amino Acids by C–H Alkylation

Contributor(s):
Hisashi Yamamoto
,
Yasushi Shimoda
Yang Q. Yang S.-D. * Lanzhou University and Lanzhou Institute of Chemical Physics, P. R. of China
Highly Efficient and Divergent Construction of Chiral γ-Phosphono-α-Amino Acids via Palladium-Catalyzed Alkylation of Unactivated C(sp3)–H Bonds.

ACS Catal. 2017;
7: 5220-5224
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Further Information

Publication History

Publication Date:
19 October 2017 (online)

 
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Key words

palladium catalysis - amino acids - alkylation

Significance

The authors have developed a highly diastereoselective synthesis of chiral γ-phosphino-α-amino acids through palladium-catalyzed C–H activation. The reaction can be carried out on a gram scale.


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Comment

Chiral γ-phosphino-α-amino acids are important motifs in various bioactive compounds. Readily available amino acid derivatives bearing a quinolin-8-yl (AQ) directing group provide the corresponding products, from which the directing AQ group can be easily removed.


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