Asymmetric Mannich reactions of (S)-N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines with yne nucleophiles

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Date
2020-10-29
Author
Li, Ziyi
Wang, Li
Huang, Yunqi
Mei, Haibo
Konno, Hiroyuki
Moriwaki, Hiroki
Soloshonok, Vadym Anatolievch ORCID
Han, Jianlin ORCID
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  Estadisticas en RECOLECTA
(LA Referencia)

Beilstein Journal of Organic Chemistry 16 : 2671-2678 (2020)
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http://hdl.handle.net/10810/50020
Abstract
In the present work, arylethynes were studied as new C-nucleophiles in the asymmetric Mannich addition reactions with (S)-N-tert-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
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This is an Open Access article under the terms of the Creative Commons Attribution License (CC BY 4.0)
Except where otherwise noted, this item's license is described as This is an Open Access article under the terms of the Creative Commons Attribution License (CC BY 4.0)