通过O-高烯丙基羟胺的串联芳基化反应实现钯催化的N-芳基-3-芳基甲基异恶唑烷的高度立体选择性合成。
Palladium-catalyzed highly stereoselective synthesis of N-aryl-3-arylmethylisoxazolidines via tandem arylation of O-homoallylhydroxylamines.
作者信息
Peng Jinsong, Lin Wenqing, Yuan Shixue, Chen Yuanwei
机构信息
Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
出版信息
J Org Chem. 2007 Apr 13;72(8):3145-8. doi: 10.1021/jo0625958. Epub 2007 Mar 17.
The palladium-catalyzed tandem arylation of O-homoallylhydroxylamines with 2 equiv of aryl bromides was examined. With Pd2(dba)3 (1 mol %) as the catalyst, Xantphos (2 mol %) as the ligand, and NaOt-Bu as the base, the reactions of O-homoallylhydroxylamines with aryl bromides via sequential N-arylation/cyclization/C-arylation in toluene afforded the corresponding N-aryl-3-arylmethylisoxazolidines in good yields with excellent diastereoselectivity.
考察了钯催化的O-高烯丙基羟胺与2当量芳基溴的串联芳基化反应。以Pd2(dba)3（1 mol%）为催化剂、Xantphos（2 mol%）为配体、叔丁醇钠为碱，O-高烯丙基羟胺与芳基溴在甲苯中通过连续的N-芳基化/环化/C-芳基化反应，以良好的产率和优异的非对映选择性得到相应的N-芳基-3-芳基甲基异恶唑烷。
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