Asymmetric Mannich Reactions of ()---butylsulfinyl-3,3,3-trifluoroacetaldimines with Yne Nucleophiles

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2020 Nov 12

PMID 33178357

Citations 1

Authors

Ziyi Li

Li Wang

Yunqi Huang

Haibo Mei

Hiroyuki Konno

Hiroki Moriwaki

Vadim A Soloshonok

Jianlin Han

Affiliations

Soon will be listed here.

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.

Citing Articles

Synthesis of Aminoalkyl Sclareolide Derivatives and Antifungal Activity Studies.

Li Z, Gao H, Mei H, Wu G, Soloshonok V, Han J Molecules. 2023; 28(10).

PMID: 37241807 PMC: 10223150. DOI: 10.3390/molecules28104067.

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