Aromatic-Amide-Derived Nonbiaryl Atropisomer as Highly Efficient Ligand for Asymmetric Silver-Catalyzed [3 + 2] Cycloaddition,ACS Catalysis

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Aromatic-Amide-Derived Nonbiaryl Atropisomer as Highly Efficient Ligand for Asymmetric Silver-Catalyzed [3 + 2] Cycloaddition
ACS Catalysis ( IF 11.3 ) Pub Date : 2015-09-10 00:00:00 , DOI: 10.1021/acscatal.5b01685
Xing-Feng Bai _{1,

2} , Zheng Xu ₂ , Chun-Gu Xia ₁ , Zhan-Jiang Zheng ₂ , Li-Wen Xu _{1,

2}

Affiliation

In this work, we have successfully determined that the aromatic amide-derived nonbiaryl atropisomer/silver complex (silver-Xing-Phos) is an effective catalyst system for the solvent-dependent exo-selective cycloaddition of glycine aldimino esters with chalcones or less-reactive methyl cinnamates to give the corresponding chalcone- or cinnamate-derived pyrrolidines with multiple stereogenic centers in good yields and high diastereoselectivities as well as excellent enantioselectivities. Remarkably, it is the first example of highly enantioselective silver-catalyzed [3 + 2] cycloaddition of methyl cinnamates with glycine aldimino esters.

中文翻译：

芳酰胺衍生的壬二芳基阻转异构体作为不对称银催化的[3 + 2]环加成反应的高效配体

在这项工作中，我们已经成功地确定了芳族酰胺衍生的阻转异构体nonbiaryl /银复合物（银性-PHOS）是用于从属溶剂有效的催化剂体系外的甘氨酸与醛亚查耳酮或更低反应性的酯-选择性环加成肉桂酸甲酯可得到具有多个立体异构中心的相应查尔酮或肉桂酸酯衍生的吡咯烷，收率高，非对映选择性高，对映选择性高。值得注意的是，这是肉桂酸甲酯与甘氨酸醛二氨基酸酯高度对映选择性银催化的[3 + 2]环加成反应的第一个实例。

更新日期：2015-09-10

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