Departamento de Química Orgánica (Módulo 1), Facultad de Ciencias, Universidad Autónoma de Madrid, 28049-Madrid, Spain.
EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, Fife, Scotland, KY16 9ST, UK.
Chem Commun (Camb). 2022 Jun 28;58(52):7277-7280. doi: 10.1039/d2cc02432b.
The photocatalytic generation of α-amino radicals is combined with chiral isothiourea derived α,β-unsaturated acyl ammonium intermediates. The reaction proceeds a [3+2] radical-polar crossover mechanism to generate γ-lactams in good yields and enantioselectivities. The enantioselective radical conjugate addition was carried out under batch and flow conditions.
α-氨基自由基的光催化生成与手性异硫脲衍生的α,β-不饱和酰基铵中间体相结合。反应通过[3+2]自由基-极性交叉机制进行,以良好的产率和对映选择性生成γ-内酰胺。对映选择性自由基共轭加成在分批和流动条件下进行。