期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 21, 页码 14308-14318出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01774
关键词
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资金
- Agencia Estatal Investigacion of Spain (AEI) [RTI2018-099592-B-C21, RTI2018-099592-B- C22]
- EU [956544]
- Universidad de La Rioja
- Marie Curie Actions (MSCA) [956544] Funding Source: Marie Curie Actions (MSCA)
This research describes the diastereoselective 1,4-conjugate additions of anionic and radical C-nucleophiles to a chiral bicyclic dehydroalanine (Dha). Notably, radical carbon photolysis using a metal-free photocatalyst through a catalytic photoredox process provides exceptional yields and selectivities at room temperature. These 1,4-conjugate additions serve as an excellent starting point for synthesizing enantiomerically pure carbon-beta-substituted unnatural alpha-amino acids (UAAs), with potential applications in chemical biology.
-and diastereoselective 1,4-conjugate addi-tions of anionic and radical C-nucleophiles to a chiral bicyclic dehydroalanine (Dha) are described. Of particular importance, radical carbon photolysis by a catalytic photoredox process using a simple method with a metal-free photocatalyst provides exceptional yields and selectivities at room temperature. Moreover, these 1,4-conjugate additions offer an excellent starting point for synthesizing enantiomerically pure carbon-beta-substituted unnatural alpha-amino acids (UAAs), which could have a high potential for applications in chemical biology.
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