Liu Renmao, Herron Steven R, Fleming Steven A
Department of Chemistry, Brigham Young University, Provo, UT 84602, USA.
J Org Chem. 2007 Jul 20;72(15):5587-91. doi: 10.1021/jo0705014. Epub 2007 Jun 27.
Aziridines were formed by copper-catalyzed intramolecular nitrene addition to alkenes. The carbamate group was used as the tether between the alkene and the nitrene. Subsequent nucleophilic attack of the aziridine was accomplished using RSH, R2NH, N3-, or ROH as the nucleophile. This addition was found to be regio- and stereoselective. This methodology has been used to demonstrate its utility in the regio- and stereoselective synthesis of a 1,2-diamino-3-hydroxycyclohexane. This substitution pattern is found in natural products such as Tamiflu.
氮丙啶是通过铜催化分子内氮烯加成到烯烃上形成的。氨基甲酸酯基团用作烯烃和氮烯之间的连接基团。随后，使用RSH、R2NH、N3-或ROH作为亲核试剂完成氮丙啶的亲核攻击。发现这种加成具有区域选择性和立体选择性。该方法已被用于证明其在1,2-二氨基-3-羟基环己烷的区域和立体选择性合成中的实用性。这种取代模式存在于如达菲等天然产物中。
