Smith Matthew J S, Tu Wenbin, Robertson Craig M, Bower John F
Department of Chemistry, University of Liverpool, Crown Street, Liverpool, L69 7ZD, UK.
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
Angew Chem Int Ed Engl. 2023 Nov 27;62(48):e202312797. doi: 10.1002/anie.202312797. Epub 2023 Oct 27.
Under acidic reaction conditions (TFA), deprotection of BocNR(OSO R) reagents triggers intermolecular aminative cyclizations of alkenes equipped with pendant nucleophiles. The processes are predicated on a sequence of stereospecific intermolecular aza-Prilezhaev aziridination followed by stereospecific S 2-like opening by the pendant nucleophile. The method offers broad scope with respect to the nucleophile (N-, O- or C-based), alkene and cyclization mode, allowing the installation of two contiguous stereocenters under operationally simple conditions.
在酸性反应条件下（三氟乙酸），BocNR(OSO R)试剂的脱保护引发了带有亲核侧基的烯烃的分子间胺化环化反应。这些过程基于一系列立体专一性的分子间氮杂-Prilezhaev氮丙啶化反应，随后是亲核侧基进行的类似立体专一性S 2的开环反应。该方法在亲核试剂（基于N、O或C）、烯烃和环化模式方面具有广泛的适用范围，能够在操作简单的条件下构建两个相邻的立体中心。
