Highly Efficient and Divergent Construction of Chiral gamma-Phosphono-alpha-Amino Acids via Palladium-Catalyzed Alkylation of Unactivated C(sp(3))-H Bonds | |
Department | OSSO国家重点实验室 |
Yang, Qiang1; Yang SD(杨尚东)1,2; Yang SD(杨尚东) | |
2017 | |
Source Publication | ACS Catalysis |
ISSN | 2155-5435 |
Volume | 7Issue:8Pages:5220-5224 |
Abstract | 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. |
Keyword | C-h Activation Gamma-phosphono-alpha-amino Acids Alkylation Palladium Synthetic Methods |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1021/acscatal.7b01779 |
Funding Organization | the NSFC (Nos. 21472076;21532001);PCSIRT (Nos. IRT_15R28;lzujbky-2016-ct02) |
Indexed By | SCI |
If | 10.614 |
Language | 英语 |
compositor | 第二作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/22452 |
Collection | 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Yang SD(杨尚东) |
Affiliation | 1.Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China 2.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China |
Recommended Citation GB/T 7714 | Yang, Qiang,Yang SD,Yang SD. Highly Efficient and Divergent Construction of Chiral gamma-Phosphono-alpha-Amino Acids via Palladium-Catalyzed Alkylation of Unactivated C(sp(3))-H Bonds[J]. ACS Catalysis,2017,7(8):5220-5224. |
APA | Yang, Qiang,Yang SD,&杨尚东.(2017).Highly Efficient and Divergent Construction of Chiral gamma-Phosphono-alpha-Amino Acids via Palladium-Catalyzed Alkylation of Unactivated C(sp(3))-H Bonds.ACS Catalysis,7(8),5220-5224. |
MLA | Yang, Qiang,et al."Highly Efficient and Divergent Construction of Chiral gamma-Phosphono-alpha-Amino Acids via Palladium-Catalyzed Alkylation of Unactivated C(sp(3))-H Bonds".ACS Catalysis 7.8(2017):5220-5224. |
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acscatal.7b01779.pdf(2021KB) | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | View Application Full Text |
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