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Rh II ‐Catalyzed [3+2] Cycloaddition of 2 H ‐Azirines with N ‐Sulfonyl‐1,2,3‐Triazoles
Author(s) -
Zhao YunZhou,
Yang HaiBin,
Tang XiangYing,
Shi Min
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406460
Subject(s) - cycloaddition , synthon , carbene , chemistry , sulfonyl , catalysis , medicinal chemistry , rhodium , stereochemistry , organic chemistry , alkyl
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).