A Chiral Secondary Amine-Amidophosphane Precatalyst for Silver-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions
A Chiral Secondary Amine-Amidophosphane Precatalyst for Silver-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions
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银催化不对称 1,3-偶极环加成反应的手性仲胺-氨基膦预催化剂
DOI：
10.1055/s-0037-1609492
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发表时间：
2018
期刊：
影响因子：
--
通讯作者：
Wang Haifei
中科院分区：
文献类型：
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作者：
Zheng Xiaojun;Deng Qifu;Hou Qinglin;Zhang Kaiqiang;Wen Pushan;Hu Shunqin;Wang Haifei
以手性1，2-二苯基乙二胺和天然α-氨基酸为原料合成了一类多功能氨基膦。其中，与银（I）盐组合，手性仲胺-酰胺基膦预催化剂已被证明是偶氮甲碱叶立德的不对称1，3-偶极环加成中的高效多功能预催化剂，所述叶立德包括一系列杂环、脂族和2-取代的偶氮甲碱叶立德，以及芳族α，β-不饱和醛衍生的亚氨基酯与不同缺电子烯烃，以及以N，N′-二异丙基碳二亚胺为脱水剂原位生成的α-亚氨基酯的三组分反应。在最佳条件下，以较高的收率（高达99%）和对映选择性（高达> 99.9%ee）得到了高度官能化的内加合物。
A class of multifunctional amidophosphanes derived from chiral 1,2-diphenylethylenediamines and natural α-amino acids has been developed. Among these, in combination with silver(I) salts, a chiral secondary amine–amidophosphane precatalyst has been demonstrated as being a highly efficient multifunctional precatalyst in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides, including a series of heterocyclic, aliphatic, and 2-substituted azomethine ylides, and aromatic α,β-unsaturated aldehyde derived imino esters with different electron-deficient alkenes, as well as the three-component reaction of α-imino esters generated in situ by usingN,N′-diisopropylcarbodiimide as dehydrating agent. Under optimal conditions, highly functionalizedendo-adducts were obtained in high to excellent yields (up to 99% yield) and enantioselectivities (up to >99.9% ee).