Synthesis of chiral isoindolinones via asymmetric propargylation/lactamization cascade. Issue 16 (18th April 2018)

• Record Type: Journal Article
• Authors: Meng, Jiao-Long; Jiao, Tang-Qian; Chen, Ya-Heng; Fu, Rui; Zhang, Shu-Sheng; Zhao, Qian; Feng, Chen-Guo; Lin, Guo-Qiang
• Is Part Of: Tetrahedron letters. Volume 59:Issue 16(2018)
• Page Start: 1564
• Page End: 1567
• Publication Date: 2018-04-18
• Subjects: Propargylation -- Isoindolinone -- N-tert-butanesulfinyl imine -- Asymmetric synthesis -- Cascade reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.03.024
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Easy operation, benign reaction conditions and high diastereoselectivity. A practical and efficient method for the synthesis of chiral isoindolinones. Versatile transformations associated with the resulting products. Abstract: A Zn-mediated propargylation/lactamization cascade reaction with chiral 2-formylbenzoate derived N - tert -butanesulfinyl imines was realized, which provided a practical and efficient method for the synthesis of chiral isoindolinones. High diastereoselectivities (up to 97:3 dr) and good reaction yields were observed for most examined cases.