Diastereo- and enantioselective intramolecular 1, 6-C–H insertion reactions of α-diazo esters catalyzed by chiral dirhodium(II) carboxylates. Issue 11 (11th March 2015)

• Record Type: Journal Article
• Authors: Ito, Motoki; Kondo, Yuji; Nambu, Hisanori; Anada, Masahiro; Takeda, Koji; Hashimoto, Shunichi
• Is Part Of: Tetrahedron letters. Volume 56:Issue 11(2015)
• Page Start: 1397
• Page End: 1400
• Publication Date: 2015-03-11
• Subjects: Asymmetric catalysis -- Dirhodium(II) complex -- C–H insertion -- α-Diazo ester -- Six-membered heterocycle; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.01.125
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The first catalytic asymmetric intramolecular 1, 6-C–H insertion reaction of α-diazo esters is described. With dirhodium(II) tetrakis[ N -phthaloyl-( S )- tert -leucinate], Rh2 ( S -PTTL)4, the C–H insertion proceeded in a chemoselective manner to give 2-alkenyltetrahydropyran-3-carboxylates with up to 95% ee and perfect cis diastereoselectivity.