3 years ago

Highly Efficient and Divergent Construction of Chiral γ-Phosphono-α-Amino Acids via Palladium-Catalyzed Alkylation of Unactivated C(sp3)–H Bonds

Highly Efficient and Divergent Construction of Chiral γ-Phosphono-α-Amino Acids via Palladium-Catalyzed Alkylation of Unactivated C(sp3)–H Bonds
Shang-Dong Yang, Qiang Yang
Chiral γ-phosphono-α-amino acids play a crucial role in inhibitors of natural enzymes, as well as agonists and antagonists of metabotropic glutamate receptors. In this paper, an efficient and general protocol for the construction of chiral γ-phosphono-α-amino acids via Pd-catalyzed AQ-directed C(sp3)–H alkylation of α-amino acid derivatives is developed. The reaction shows reactivity between methylene C(sp3)–H bonds with phosphonated alkyl iodides with high yields, enantioselectivity, and diastereomeric ratios, which enables access to a wide range of challenging and important γ-phosphono-α-amino acids in large scale. Meanwhile, δ-phosphono-α-amino acid and δ-phosphono-propionic acid derivatives can also be successfully obtained. The derivatization reaction in the synthesis of l-AP4 and l-phosphinothricin highlight the applicability of this method.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b01779

DOI: 10.1021/acscatal.7b01779

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