Shahedi Mansour, Omidi Niloofar, Habibi Zohreh, Yousefi Maryam, Brask Jesper, Notash Behrouz, Mohammadi Mehdi
Department of Organic Chemistry, Shahid Beheshti University, 1983969411 Tehran, Iran.
Nanobiotechnology Research Center, Avicenna Research Institute, ACECR, Tehran, Iran.
Org Biomol Chem. 2023 Mar 29;21(13):2742-2747. doi: 10.1039/d2ob02294j.
Highly functionalized pyrrolidine-2,3-diones can be synthesized efficiently and stereoselectively under mild conditions using a biocatalytic approach. The reaction led to the formation of new all-carbon quaternary stereocenters from laccase (Novozym 51003) catalyzed oxidation of catechols to -quinones and subsequent 1,4-addition with 3-hydroxy-1,5-dihydro-2-pyrrol-2-ones. The reaction was conducted with various substituents on both reactants, resulting in 13 products in moderate to good yields (42-91%). The same 15 reactions were also tested with KFe(CN) as a catalyst, but here only one reaction resulted in a product (60% yield).
使用生物催化方法，可以在温和条件下高效且立体选择性地合成高度官能化的吡咯烷 - 2,3 - 二酮。该反应通过漆酶（诺维信51003）催化邻苯二酚氧化为对醌，随后与3 - 羟基 - 1,5 - 二氢 - 2 - 吡咯 - 2 - 酮进行1,4 - 加成，从而形成新的全碳季立体中心。在两种反应物上带有各种取代基进行该反应，得到13种产物，产率中等至良好（42 - 91%）。还用KFe(CN)作为催化剂测试了相同的15个反应，但在此仅一个反应得到了产物（产率60%）。
