Asymmetric Synthesis of Polysubstituted 4-Amino- and 3,4-Diaminochromanes with a Chiral Multifunctional Organocatalyst
Asymmetric Synthesis of Polysubstituted 4-Amino- and 3,4-Diaminochromanes with a Chiral Multifunctional Organocatalyst
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手性多功能有机催化剂不对称合成多取代4-氨基和3,4-二氨基苯并二氢吡喃
DOI：
10.1021/ol300798t
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发表时间：
2012-05-04
期刊：
影响因子：
5.2
通讯作者：
Peng, Yungui
中科院分区：
文献类型：
--
作者：
Hou, Wenduan;Zheng, Bo;Peng, Yungui
开发了一系列具有两个手性环己二胺单元的多功能催化剂，并成功应用于水杨醛亚胺与硝基烯烃的不对称oxa-Michael-aza-Henry级联反应。该方法提供了一种简单有效的方法来制备具有三个连续立构中心的多取代手性4-氨基苯并吡喃，并且具有高收率（高达97%）和优异的立体选择性（高达98%ee和>99：1 dr）。还得到了非对称光学纯的3，4-二氨基苯并二氢吡喃。
A series of multifunctional catalysts with two chiral diaminocyclohexane units were developed and successfully applied in the asymmetric oxa-Michael-aza-Henry cascade reaction of salicylaldimines with nitroolefins. This approach provides a simple and efficient entry to polysubstituted chiral 4-aminobenzopyrans with three consecutive stereocenters and in high yield (up to 97%) with excellent stereoselectivity (up to 98% ee and >99:1 dr). Facile access to the nonsymmetric optically pure 3,4-diaminochromanes was also obtained.