Benzofulvenes in Trienamine Catalysis: Stereoselective Spiroindene Synthesis
Benzofulvenes in Trienamine Catalysis: Stereoselective Spiroindene Synthesis
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DOI：
10.1002/anie.201605079
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发表时间：
2016-09-05
影响因子：
16.6
通讯作者：
Jorgensen, Karl Anker
中科院分区：
文献类型：
--
作者：
Donslund, Bjarke S.;Nielsen, Rune Pagh;Jorgensen, Karl Anker
本文报道了苯并富烯与2，4-二烯醛在三烯胺催化下不对称生成含四个相邻立构中心的螺茚。苯并富烯核被认为是一个很好的起点，通过正式的环加成途径合成感兴趣的螺茚。该反应是由二苯基脯氨醇硅醚催化剂介导的，并以高产率和优异的立体选择性得到了各种各样的螺茚。所开发的系统的一个有吸引力的功能是多样化的产品支架显着通过进一步操纵的手性螺茚的可能性。因此，在有机催化步骤之后的三个分子内闭环反应导致高度复杂的多环系统。
The asymmetric formation of spiroindenes containing up to four contiguous stereocenters from the reaction of benzofulvenes with 2,4-dienals through trienamine catalysis is described. The benzofulvene core was found to be an excellent starting point for the synthesis of interesting spiroindenes through a formal cycloaddition pathway. The reaction was mediated by a diphenylprolinol silyl ether catalyst, and a diverse array of spiroindenes were obtained in high yields with excellent stereoselectivity. An attractive feature of the developed system is the possibility to diversify the product scaffold significantly by further manipulation of the chiral spiroindenes. Thus, three intramolecular ring-closing reactions following the organocatalytic step resulted in highly complex polycyclic systems.