ChemInform Abstract: General Approach to Nitrogen‐Bridged Bicyclic Frameworks by Rh‐Catalyzed Formal Carbenoid Insertion into an Amide C—N Bond. Issue 9 (February 2016)

• Record Type: Journal Article
• Authors: Harada, Shingo; Kono, Masato; Nozaki, Tomoyuki; Menjo, Yasuhiro; Nemoto, Tetsuhiro; Hamada, Yasumasa
• Is Part Of: ChemInform. Volume 47:Issue 9(2016)
• Page Start: no
• Page End: no
• Publication Date: 2016-02
• Subjects: bridged compounds (heterocyclic compounds) -- ring closure reactions, annulation reactions -- catalysis, phase‐transfer catalysis -- insertion reactions; Chemistry -- Abstracts -- Periodicals; 540.5
• DOI: 10.1002/chin.201609127
• Languages: English
• ISSNs: 0931-7597

Abstract

Abstract: The Rh‐catalyzed formal carbenoid insertion into an amide C—N bond delivers azabicyclo[X.Y.Z.]alkane derivatives in good to high yields and proceeds via the formation of Rh‐associated N‐ylides, followed by an acyl group‐selective Stevens [1, 2]‐shift through a concerted addition/elimination process on the sp 2 ‐hybridized carbon.