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手性 '-二氧化物/Mg(OTf) 配合物催化生成的铵盐的不对称 [2,3] 重排反应。

Chiral ,'-dioxide/Mg(OTf) complex-catalyzed asymmetric [2,3]-rearrangement of generated ammonium salts.

作者信息

Lin Qianchi, Hu Bowen, Xu Xi, Dong Shunxi, Liu Xiaohua, Feng Xiaoming

机构信息

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu 610064 China

出版信息

Chem Sci. 2020 Feb 19;11(11):3068-3073. doi: 10.1039/c9sc06342k.

Abstract

Catalytic enantioselective [2,3]-rearrangements of generated ammonium ylides from glycine pyrazoleamides and allyl bromides were achieved by employing a chiral ,'-dioxide/Mg complex as the catalyst. This protocol provided a facile and efficient synthesis route to a series of -α-amino acid derivatives in good yields with high stereoselectivities. Moreover, a possible catalytic cycle was proposed to illustrate the reaction process and the origin of stereoselectivity.

摘要

通过使用手性双噁唑啉/镁配合物作为催化剂,实现了甘氨酸吡唑酰胺与烯丙基溴生成的铵叶立德的催化对映选择性[2,3]重排反应。该方法为一系列α-氨基酸衍生物提供了一条简便高效的合成路线,产率良好,立体选择性高。此外,还提出了一个可能的催化循环来阐明反应过程和立体选择性的起源。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c81/8157646/ea5d4fa2b63d/c9sc06342k-s1.jpg

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