Beaver Matthew G, Buscagan Trixia M, Lavinda Olga, Woerpel K A
Amgen, 360 Binney Street, Cambridge, MA, 02142, USA.
Department of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, MNC 101-20, Pasadena, CA, 91125, USA.
Angew Chem Int Ed Engl. 2016 Jan 26;55(5):1816-9. doi: 10.1002/anie.201507806. Epub 2016 Jan 6.
Nucleophilic attack on seven-membered-ring oxocarbenium ions is generally highly stereoselective. The preferred mode of nucleophilic attack forms the product in a conformation that minimizes transannular interactions, thus leading to different stereoselectivity as compared to that of reactions involving six-membered-ring oxocarbenium ions.
对七元环氧化碳鎓离子的亲核进攻通常具有高度的立体选择性。亲核进攻的优选模式形成的产物具有一种构象,该构象使跨环相互作用最小化,因此与涉及六元环氧化碳鎓离子的反应相比,导致不同的立体选择性。