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（）-丁基亚磺酰基-3,3,3-三氟乙醛亚胺与炔亲核试剂的不对称曼尼希反应。

Asymmetric Mannich reactions of ()---butylsulfinyl-3,3,3-trifluoroacetaldimines with yne nucleophiles.

作者信息

Li Ziyi, Wang Li, Huang Yunqi, Mei Haibo, Konno Hiroyuki, Moriwaki Hiroki, Soloshonok Vadim A, Han Jianlin

机构信息

Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu, China.

Department of Biological Engineering, Graduate School of Science and Engineering, Yamagata University, Yonezawa, Yamagata 992-8510, Japan.

出版信息

Beilstein J Org Chem. 2020 Oct 29;16:2671-2678. doi: 10.3762/bjoc.16.217. eCollection 2020.

DOI:10.3762/bjoc.16.217
PMID:33178357
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7607431/
Abstract

In the present work, arylethynes were studied as new C-nucleophiles in the asymmetric Mannich addition reactions with ()---butylsulfinyl-3,3,3-trifluoroacetaldimine. The reactions were conducted under operationally convenient conditions affording the corresponding Mannich adducts with up to 87% yield and 70:30 diastereoselectivity. The isomeric products can be separated using regular column chromatography to afford diastereomerically pure compounds. The purified Mannich addition products were deprotected to give the target enantiomerically pure trifluoromethylpropargylamines. A mechanistic rationale for the observed stereochemical outcome is discussed.

摘要

在本研究中，将芳基乙炔作为新型碳亲核试剂，用于与（）-丁基亚磺酰基-3,3,3-三氟乙醛亚胺的不对称曼尼希加成反应。反应在操作简便的条件下进行，得到相应的曼尼希加合物，产率高达87%，非对映选择性为70:30。可以使用常规柱色谱法分离异构体产物，以得到非对映体纯的化合物。将纯化后的曼尼希加成产物脱保护，得到目标对映体纯的三氟甲基炔丙胺。讨论了所观察到的立体化学结果的机理依据。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39af/7607431/d9fd2c3a3348/Beilstein_J_Org_Chem-16-2671-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39af/7607431/b0f9c7e75925/Beilstein_J_Org_Chem-16-2671-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39af/7607431/5f294b8d483a/Beilstein_J_Org_Chem-16-2671-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39af/7607431/967a8f9cc9d6/Beilstein_J_Org_Chem-16-2671-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39af/7607431/4a4710fcdfba/Beilstein_J_Org_Chem-16-2671-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39af/7607431/22a47b10c446/Beilstein_J_Org_Chem-16-2671-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39af/7607431/2bb2ba8cd8f3/Beilstein_J_Org_Chem-16-2671-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39af/7607431/d9fd2c3a3348/Beilstein_J_Org_Chem-16-2671-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39af/7607431/b0f9c7e75925/Beilstein_J_Org_Chem-16-2671-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39af/7607431/5f294b8d483a/Beilstein_J_Org_Chem-16-2671-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39af/7607431/967a8f9cc9d6/Beilstein_J_Org_Chem-16-2671-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39af/7607431/4a4710fcdfba/Beilstein_J_Org_Chem-16-2671-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39af/7607431/22a47b10c446/Beilstein_J_Org_Chem-16-2671-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39af/7607431/2bb2ba8cd8f3/Beilstein_J_Org_Chem-16-2671-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39af/7607431/d9fd2c3a3348/Beilstein_J_Org_Chem-16-2671-g008.jpg

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