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

dc.contributor.authorLi, Ziyi
dc.contributor.authorWang, Li
dc.contributor.authorHuang, Yunqi
dc.contributor.authorMei, Haibo
dc.contributor.authorKonno, Hiroyuki
dc.contributor.authorMoriwaki, Hiroki
dc.contributor.authorSoloshonok, Vadym Anatolievch ORCID
dc.contributor.authorHan, Jianlin ORCID
dc.date.accessioned2021-02-04T09:28:43Z
dc.date.available2021-02-04T09:28:43Z
dc.date.issued2020-10-29
dc.identifier.citationBeilstein Journal of Organic Chemistry 16 : 2671-2678 (2020)es_ES
dc.identifier.issn1860-5397
dc.identifier.urihttp://hdl.handle.net/10810/50020
dc.description.abstractIn 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 discussedes_ES
dc.description.sponsorshipWe gratefully acknowledge the financial support from the National Natural Science Foundation of China (No. 21761132021) and Qing Lan Project of Jiangsu Province. IKERBASQUE, Basque Foundation for Science (for V. A. Soloshonok) is also acknowledged.es_ES
dc.language.isoenges_ES
dc.publisherBeilstein-Institutes_ES
dc.rightsinfo:eu-repo/semantics/openAccesses_ES
dc.rights.urihttp://creativecommons.org/licenses/by/3.0/es/*
dc.subjectarylethyneses_ES
dc.subjectasymmetric Mannich reactiones_ES
dc.subjectC-nucleophilees_ES
dc.subjectCF3-aldiminees_ES
dc.subjectfluorinated propargylaminees_ES
dc.subjectquaternary stereogenic centerses_ES
dc.subjectself-disproportionationes_ES
dc.subjectmedicinal chemistryes_ES
dc.subjectfluorinees_ES
dc.subjectenantiomerses_ES
dc.subjectaccesses_ES
dc.subjectpharmaceuticalses_ES
dc.subjectconstructiones_ES
dc.subjectalkynylationes_ES
dc.subjectderivativeses_ES
dc.titleAsymmetric Mannich reactions of (S)-N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines with yne nucleophileses_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.rights.holderThis is an Open Access article under the terms of the Creative Commons Attribution License (CC BY 4.0)es_ES
dc.rights.holderAtribución 3.0 España*
dc.relation.publisherversionhttps://pubmed.ncbi.nlm.nih.gov/33178357/es_ES
dc.identifier.doi10.3762/bjoc.16.217
dc.departamentoesQuímica orgánica Ies_ES
dc.departamentoeuKimika organikoa Ies_ES


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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)