Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706, USA.
Angew Chem Int Ed Engl. 2010 Jul 26;49(32):5529-32. doi: 10.1002/anie.200906342.
Allylic sulfamides undergo efficient aerobic oxidative cyclization at room temperature, mediated by a new Pd catalyst system consisting of 5% Pd(TFA)/10% DMSO in THF. The synthetic utility of these reactions is enhanced by several features: (1) the sulfamide substrates are accessible in multi-gram scale from the corresponding allylic and primary amines, (2) the cyclic sulfamide products are readily converted to the corresponding 1,2-diamines upon treatment with LiAlH, and (3) substrates derived from chiral allylic amines cyclize with very high levels of diastereoselectivity.
烯丙基磺酰胺在室温下经新型 Pd 催化剂体系(由 5% Pd(TFA)/10% DMSO 在 THF 中组成)作用下可高效进行有氧氧化环化反应。这些反应具有以下几个特点,增强了其合成实用性:(1)磺酰胺底物可由相应的烯丙基和伯胺经多克规模制备得到;(2)环状磺酰胺产物经 LiAlH 处理可轻易转化为相应的 1,2-二胺;(3)手性烯丙基胺衍生的底物环化反应具有很高的非对映选择性。