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- Publisher Website: 10.1038/s41557-023-01362-3
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Article: Modular and diverse synthesis of amino acids via asymmetric decarboxylative protonation of aminomalonic acids
Title | Modular and diverse synthesis of amino acids via asymmetric decarboxylative protonation of aminomalonic acids |
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Authors | |
Issue Date | 16-Nov-2023 |
Publisher | Nature Research |
Citation | Nature Chemistry, 2023, v. 15, n. 12, p. 1672-1682 How to Cite? |
Abstract | Stereoselective protonation is a challenge in asymmetric catalysis. The small size and high rate of transfer of protons mean that face-selective delivery to planar intermediates is hard to control, but it can unlock previously obscure asymmetric transformations. Particularly, when coupled with a preceding decarboxylation, enantioselective protonation can convert the abundant acid feedstocks into structurally diverse chiral molecules. Here an anchoring group strategy is demonstrated as a potential alternative and supplement to the conventional structural modification of catalysts by creating additional catalyst–substrate interactions. We show that a tailored benzamide group in aminomalonic acids can help build a coordinated network of non-covalent interactions, including hydrogen bonds, π–π interactions and dispersion forces, with a chiral acid catalyst. This allows enantioselective decarboxylative protonation to give α-amino acids. The malonate-based synthesis introduces side chains via a facile substitution of aminomalonic esters and thus can access structurally and functionally diverse amino acids. |
Persistent Identifier | http://hdl.handle.net/10722/340655 |
ISSN | 2023 Impact Factor: 19.2 2023 SCImago Journal Rankings: 6.940 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Zheng, Wei-Feng | - |
dc.contributor.author | Chen, Jingdan | - |
dc.contributor.author | Qi, Xiaotian | - |
dc.contributor.author | Huang, Zhongxing | - |
dc.date.accessioned | 2024-03-11T10:46:11Z | - |
dc.date.available | 2024-03-11T10:46:11Z | - |
dc.date.issued | 2023-11-16 | - |
dc.identifier.citation | Nature Chemistry, 2023, v. 15, n. 12, p. 1672-1682 | - |
dc.identifier.issn | 1755-4330 | - |
dc.identifier.uri | http://hdl.handle.net/10722/340655 | - |
dc.description.abstract | <p>Stereoselective protonation is a challenge in asymmetric catalysis. The small size and high rate of transfer of protons mean that face-selective delivery to planar intermediates is hard to control, but it can unlock previously obscure asymmetric transformations. Particularly, when coupled with a preceding decarboxylation, enantioselective protonation can convert the abundant acid feedstocks into structurally diverse chiral molecules. Here an anchoring group strategy is demonstrated as a potential alternative and supplement to the conventional structural modification of catalysts by creating additional catalyst–substrate interactions. We show that a tailored benzamide group in aminomalonic acids can help build a coordinated network of non-covalent interactions, including hydrogen bonds, <em>π</em>–<em>π</em> interactions and dispersion forces, with a chiral acid catalyst. This allows enantioselective decarboxylative protonation to give α-amino acids. The malonate-based synthesis introduces side chains via a facile substitution of aminomalonic esters and thus can access structurally and functionally diverse amino acids.</p> | - |
dc.language | eng | - |
dc.publisher | Nature Research | - |
dc.relation.ispartof | Nature Chemistry | - |
dc.title | Modular and diverse synthesis of amino acids via asymmetric decarboxylative protonation of aminomalonic acids | - |
dc.type | Article | - |
dc.identifier.doi | 10.1038/s41557-023-01362-3 | - |
dc.identifier.scopus | eid_2-s2.0-85176559683 | - |
dc.identifier.volume | 15 | - |
dc.identifier.issue | 12 | - |
dc.identifier.spage | 1672 | - |
dc.identifier.epage | 1682 | - |
dc.identifier.eissn | 1755-4349 | - |
dc.identifier.isi | WOS:001102938900002 | - |
dc.identifier.issnl | 1755-4330 | - |