Chiral donor−acceptor azetines as powerful reactants for synthesis of amino acid derivatives
| dc.contributor.author | Doyle, Michael | |
| dc.contributor.author | Marichev, Kostiantyn | |
| dc.contributor.author | Dong, Kuiyong | |
| dc.contributor.author | Massey, Lynée | |
| dc.contributor.author | Deng, Yongming | |
| dc.contributor.author | De Angelis, Luca | |
| dc.contributor.author | Wang, Kan | |
| dc.contributor.author | Arman, Hadi | |
| dc.date.accessioned | 2021-11-15T18:41:55Z | |
| dc.date.available | 2021-11-15T18:41:55Z | |
| dc.date.issued | 2019-11-22 | |
| dc.description.abstract | Coupling reactions of amines and alcohols are of central importance for applications in chemistry and biology. These transformations typically involve the use of a reagent, activated as an electrophile, onto which nucleophile coupling results in the formation of a carbon-nitrogen or a carbon–oxygen bond. Several promising reagents and procedures have been developed to achieve these bond forming processes in high yields with excellent stereo-control, but few offer direct coupling without the intervention of a catalyst. Herein, we report the synthesis of chiral donor–acceptor azetines by highly enantioselective [3 + 1]-cycloaddition of enoldiazoacetates with aza-ylides and their selective coupling with nitrogen and oxygen nucleophiles via 3-azetidinones to form amino acid derivatives, including those of peptides and natural products. The overall process is general for a broad spectrum of nucleophiles, has a high degree of electronic and steric selectivity, and retains the enantio-purity of the original azetine. | en_US |
| dc.description.department | Chemistry | en_US |
| dc.identifier.issn | 1476-4687 | |
| dc.identifier.uri | https://hdl.handle.net/20.500.12588/715 | |
| dc.language.iso | en_US | en_US |
| dc.publisher | Nature | en_US |
| dc.relation.ispartofseries | Nature Communications; | |
| dc.rights | Attribution 3.0 United States | * |
| dc.rights.uri | http://creativecommons.org/licenses/by/3.0/us/ | * |
| dc.title | Chiral donor−acceptor azetines as powerful reactants for synthesis of amino acid derivatives | en_US |
| dc.type | Article | en_US |