首页 | 本学科首页   官方微博 | 高级检索  
     检索      


Chemoselectivity Control in the Reactions of 1,2‐Cyclic Sulfamidates with Amines
Authors:Dr Lara Mata  Prof Alberto Avenoza  Dr Jesús H Busto  Prof Jesús M Peregrina
Institution:Departamento de Química, Universidad de La Rioja, Centro de Investigación en Síntesis Química, Madre de Dios, 51, 26006 Logro?o (Spain), Fax: (+34)?941299620
Abstract:Although 1,2‐cyclic sulfamidates derived from α‐methylisoserine undergo nucleophilic displacement at the quaternary center, to the best of our knowledge their behavior with amines as nucleophiles has never been explored. We have found that a broad range of amines can be used, demonstrating the scope of the reaction, and that excellent control of the chemoselectivity can be achieved. Application of this methodology for the synthesis of a chiral α,β‐diamino acid and an important piperazinone heterocycle is also presented. Additionally, we have found that DMF and DMSO behave not only as polar aprotic solvents but also as Onucleophilic reagents, allowing the incorporation of an oxygen atom at a quaternary center of the electrophile, with inversion of configuration.
Keywords:amines  amino acids  chemoselectivity  nucleophilic substitution  ring‐opening reactions
设为首页 | 免责声明 | 关于勤云 | 加入收藏

Copyright©北京勤云科技发展有限公司  京ICP备09084417号