Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Pharmaceutical Engineering & Life Science , Changzhou University , Changzhou 213164 , P. R. China.
Org Lett. 2018 Apr 6;20(7):1777-1780. doi: 10.1021/acs.orglett.8b00213. Epub 2018 Mar 14.
A t-BuOCu-initiated reaction sequence of styrene borometalation and intramolecular imine addition has been achieved using a Cu(OTf)/dppf combination as catalyst. The product of this reaction cascade is a useful 2,3-disubstituted indoline bearing a versatile boryl moiety and is formed with sole cis-selectivity. To account for the observation of the exclusive formation of cis-stereoisomers, a transition state featuring copper-imine coordination is suggested. The application to the synthesis of antioxidant tetrahydroindenoindoles is described.
使用 Cu(OTf)/dppf 作为催化剂，实现了苯乙烯硼金属化和分子内亚胺加成的 t-BuOCu 引发的反应序列。该反应级联的产物是一种有用的 2,3-二取代吲哚，带有多功能硼基部分，并且具有单一的顺式选择性。为了解释观察到的顺式立体异构体的唯一形成，提出了具有铜-亚胺配位的过渡态。描述了该方法在抗氧化剂四氢茚并吲哚合成中的应用。
