Enantioselective synthesis of syn-2-amino-1,3-diols via organocatalytic sequential oxa-Michael/α-amination reactions of α,β-unsaturated aldehydes

• Published in: Tetrahedron letters Vol. 57; no. 23; pp. 2554 - 2557
• Main Authors: Weng, Jiang, Huang, Lin-Jie, Long, Liang, Xu, Ling-Yi, Lu, Gui
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 08.06.2016; Elsevier
• Subjects: 2-Amino-1,3-diol; Chemistry; Chemistry, Organic; Clavaminol H; One-pot; Organocatalysis; Physical Sciences; Safingol; Science & Technology; Safingol; One-pot; Clavaminol H; Organocatalysis; 2-Amino-1,3-diol; ANALOGS; D-ERYTHRO-SPHINGOSINE; EFFICIENT SYNTHESIS; SPHINGANINE; ALIPHATIC-ALDEHYDES; L-THREO-SPHINGOSINE; ACID-DERIVATIVES; ASYMMETRIC ALPHA-AMINATION; RIBO-PHYTOSPHINGOSINE; STEREOSELECTIVE-SYNTHESIS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2016.04.109

[Display omitted] •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. 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.