Catalytic asymmetric synthesis of (−)-E-δ-viniferin via an intramolecular C–H insertion of diaryldiazomethane using Rh2(S-TFPTTL)4. Issue 29 (15th July 2015)

• Record Type: Journal Article
• Authors: Natori, Yoshihiro; Ito, Motoki; Anada, Masahiro; Nambu, Hisanori; Hashimoto, Shunichi
• Is Part Of: Tetrahedron letters. Volume 56:Issue 29(2015)
• Page Start: 4324
• Page End: 4327
• Publication Date: 2015-07-15
• Subjects: Chiral dirhodium(II) complex -- C–H insertion -- Diaryldiazomethane -- trans-Resveratrol dimer -- E-δ-Viniferin; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.05.072
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: An asymmetric synthesis of (−)- E -δ-viniferin, a trans -resveratrol dimer natural product containing a dihydrobenzofuran ring, has been achieved by exploiting a Rh(II)-catalyzed intramolecular C–H insertion reaction of a diaryldiazomethane derivative as a key step. The C–H insertion under catalysis by dirhodium(II) tetrakis[ N -tetrafluorophthaloyl-( S )- tert -leucinate], Rh2 ( S -TFPTTL)4, provided the 2, 3-diaryl-2, 3-dihydrobenzofuran core structure with perfect cis diastereoselectivity and 96% ee.