Laboratory No. 101, Medicinal and Process Chemistry Division (MPC), CSIR-Central Drug Research Institute (CDRI) , Chattar Manzil Palace, Lucknow, Uttar Pradesh 226-001, India.
J Org Chem. 2013 Dec 6;78(23):11656-69. doi: 10.1021/jo4012249. Epub 2013 Sep 17.
A mild step and atom-economical nonepimerizing chemo- and enantioselective N-alkylating procedure has been developed via oxidation/imine-iminium formation/reduction cascade using TEMPO-BAIB-HEH-Brønsted acid catalysis in DMPU as solvent and a stoichiometric amount of amine. The optimized conditions were further extended for the nonenzymatic kinetic resolution of the chiral amine thus formed under nonenzymatic in situ hydrogen-transfer conditions using VAPOL-derived phosphoric acid (VAPOL-PA) as the Brønsted acid catalyst. The enantioselective cascade of the presented reaction was successfully utilized in the synthesis of octahydropyrazinopyridoindole and its higher ring analogues.
发展了一种温和的步骤和原子经济性的非外消旋化的化学和对映选择性 N-烷基化方法，该方法通过 TEMPO-BAIB-HEH-Brønsted 酸催化在 DMPU 溶剂中进行氧化/亚胺-亚胺鎓形成/还原级联反应，并使用化学计量的胺。优化的条件进一步扩展到在非酶原位氢转移条件下使用 VAPOL 衍生的磷酸（VAPOL-PA）作为 Brønsted 酸催化剂对形成的手性胺进行非酶动力学拆分。所提出的反应的对映选择性级联反应成功地用于八氢吡嗪并吡啶并吲哚及其更高环类似物的合成。
