Diastereo- and enantioselective cyclopropanation of alkyenyl fluorides with benzyl diazoarylacetates. Issue 14 (1st April 2015)

• Record Type: Journal Article
• Authors: Su, Yan; Bai, Miao; Qiao, Jin-Bao; Li, Xiao-Jing; Li, Rui; Tu, Yong-Qiang; Gu, Peiming
• Is Part Of: Tetrahedron letters. Volume 56:Issue 14(2015)
• Page Start: 1805
• Page End: 1807
• Publication Date: 2015-04-01
• Subjects: Cyclopropanation -- Fluorides -- Rh catalyst -- Diazo esters; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.02.044
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A catalytic diastereo- and enantiocontrolled preparation of cis -β-fluorocyclopropane carboxylates through the Rh-catalyzed cyclopropanation of alkenyl fluorides with diazoarylacetates has been realized. Rh2 ( S -DOSP)4 and benzyl diazoarylacetates were found to be beneficial to the cyclopropanation with high diastereoselectivity. Thirteen cis -β-fluorocyclopropane carboxylates were prepared in hexane at 0 °C with good to excellent yields. The enantiomeric excess was up to 97%, and the diastereomer ratio was up to 95:5.