title: Rh(II)-catalyzed [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles.
abstract: Rh(II)-catalyzed intermolecular [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles is disclosed, in which a series of fully functionalized pyrroles is produced via rhodium azavinyl carbene intermediates. A distinct feature of this reaction is that the azavinyl carbene serves as a [2 C] equivalent, instead of as [1 C] or aza-[3 C] synthons, which have been reported previously in cyclopropanations and [3+n] cycloadditions. Moreover, this methodology has also been successfully applied in the total synthesis of URB447 as well as the formal synthesis of Atorvastatin (Lipitor).
authors: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China).
authors: Yun-Zhou
authors: YZ
authors: Zhao
authors: Hai-Bin
authors: HB
authors: Yang
authors: Xiang-Ying
authors: XY
authors: Tang
authors: Min
authors: M
authors: Shi
mesh_terms: D000069059:Atorvastatin / Q000138:chemical synthesis* / Q000737:chemistry; D001389:Azirines / Q000737:chemistry*; D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D061565:Cycloaddition Reaction; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*
chemical_list: C539875:(4-amino-1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrol-3-yl)(phenyl)methanone; D001389:Azirines; D001593:Benzyl Compounds; D011758:Pyrroles; D014230:Triazoles; D000069059:Atorvastatin; D012238:Rhodium
keywords: 2 H-azirines; azavinyl carbenes; pyrroles; rhodium; triazoles