Direct Catalytic Asymmetric Vinylogous Conjugate Addition of Unsaturated Butyrolactones to α, β‐Unsaturated Thioamides1. Issue 21 (16th April 2014)

• Record Type: Journal Article
• Authors: Yin, Liang; Takada, Hisashi; Lin, Shaoquan; Kumagai, Naoya; Shibasaki, Masakatsu
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 21(2014)
• Page Start: 5327
• Page End: 5331
• Publication Date: 2014-04-16
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201402332
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Soft Lewis acid/Brønsted base cooperative catalysts have enabled direct catalytic asymmetric vinylogous conjugate addition of α, β‐ and β, γ‐unsaturated butyrolactones to α, β‐unsaturated thioamides with perfect atom economy. When using α‐angelica lactone and its derivatives as pronucleophiles, as little as 0.5 mol % catalyst loading was sufficient to complete the reaction necessary to construct consecutive tri‐ and tetrasubstituted stereogenic centers in a highly diastereo‐ and enantioselective fashion.</p> </abstract>