Stereoselective access to (Z)-α, γ-diazido-α, β-unsaturated esters via Lewis acid-mediated 1, 3-diazidation of α, α-dimethoxy-β, γ-unsaturated esters with trimethylsilyl azide. Issue 21 (20th May 2015)

• Record Type: Journal Article
• Authors: Kishii, Naomi; Negishi, Saeka; Yamada, Takeshi; Sugimura, Hideyuki
• Is Part Of: Tetrahedron letters. Volume 56:Issue 21(2015)
• Page Start: 2813
• Page End: 2816
• Publication Date: 2015-05-20
• Subjects: 1, 3-Diazidation -- Trimethylsilyl azide -- (Z)-2, 4-Diazido-2-alkenoate -- 2, 2-Dimethoxy-3-alkenoate -- Huisgen cycloaddition; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.04.047
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The synthesis of α, γ-diazido-α, β-unsaturated esters is carried out via a Lewis acid-mediated 1, 3-diazidation of α, α-dimethoxy-β, γ-unsaturated esters using two equivalents of trimethylsilyl azide. The reaction proceeds in a highly stereoselective manner to provide only the ( Z )-stereoisomers of the diazide products. The optimization and scope of the new method are discussed, and the utility of the products is demonstrated in the synthesis of bis-1, 2, 3-triazole derivatives.