Enantioselective synthesis of syn-2-amino-1, 3-diols via organocatalytic sequential oxa-Michael/α-amination reactions of α, β-unsaturated aldehydes. Issue 23 (8th June 2016)

• Record Type: Journal Article
• Authors: Weng, Jiang; Huang, Lin-Jie; Long, Liang; Xu, Ling-Yi; Lu, Gui
• Is Part Of: Tetrahedron letters. Volume 57:Issue 23(2016)
• Page Start: 2554
• Page End: 2557
• Publication Date: 2016-06-08
• Subjects: Organocatalysis -- One-pot -- 2-Amino-1, 3-diol -- Safingol -- Clavaminol H; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.04.109
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A one-pot sequential oxa-Michael/α-amination reaction has been described. Highly enantioenriched syn -β, γ-functional alcohols were obtained. (+)-Safingol and d - threo -clavaminol H were prepared with this method as key step. Abstract: A general and efficient method for the enantioselective synthesis of syn -2-amino-1, 3-diols is reported. It involves the methodology of secondary amine-catalyzed one-pot sequential oxa-Michael/α-amination reactions of α, β-unsaturated aldehydes. This method has also been successfully applied to highly efficient total syntheses of (+)-safingol and d - threo -clavaminol H with excellent stereoselectivities.