钯催化的源自氨基磺酸酯亚胺的1-氮杂二烯与螺环环戊烷的对映选择性和区域选择性（3 + 2）环加成反应。
Palladium-catalysed enantio- and regioselective (3 + 2) cycloaddition reactions of sulfamidate imine-derived 1-azadienes towards spirocyclic cyclopentanes.
作者信息
Pham Quoc Hoang, Tague Andrew J, Richardson Christopher, Gardiner Michael G, Pyne Stephen G, Hyland Christopher J T
机构信息
School of Chemistry and Molecular Bioscience, Molecular Horizons Research Institute, University of Wollongong Wollongong 2522 New South Wales Australia
Research School of Chemistry, The Australian National University Canberra 2601 Australia.
出版信息
Chem Sci. 2023 Apr 18;14(18):4893-4900. doi: 10.1039/d3sc01510f. eCollection 2023 May 10.
An enantio- and diastereoselective Pd-catalysed (3 + 2) cycloaddition of bis(trifluoroethyl) 2-vinyl-cyclopropane-1,1-dicarboxylate (VCP) with cyclic sulfamidate imine-derived 1-azadienes (SDAs) has been developed. These reactions provide highly functionalized spiroheterocycles having three contiguous stereocentres, including a tetrasubstituted carbon bearing an oxygen functionality. The two geminal trifluoroethyl ester moieties can be manipulated in a facially selective manner to afford more diversely decorated spirocycles with four contiguous stereocentres. In addition, diastereoselective reduction of the imine moiety can also afford a fourth stereocentre and exposes the important 1,2-amino alcohol functionality.
已开发出一种对映体和非对映体选择性的钯催化双（三氟乙基）2-乙烯基环丙烷-1,1-二羧酸酯（VCP）与环状亚磺酰胺亚胺衍生的1-氮杂二烯（SDA）的（3 + 2）环加成反应。这些反应提供了具有三个相邻立体中心的高度官能化螺杂环，包括一个带有氧官能团的四取代碳。两个偕三氟乙酯部分可以以面选择性方式进行操作，以提供具有四个相邻立体中心的装饰更为多样的螺环。此外，亚胺部分的非对映体选择性还原还可以产生第四个立体中心，并暴露出重要的1,2-氨基醇官能团。
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