Premium
Yb(OTf) 3 ‐ or Au I ‐Catalyzed Domino Intramolecular Hydroamination and Ring‐Opening of Sulfonamide‐Substituted 1,1‐Vinylidenecyclopropanediesters
Author(s) -
Wu Lei,
Shi Min
Publication year - 2011
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.201102159
Subject(s) - hydroamination , sulfonamide , intramolecular force , moiety , alkyne , lewis acids and bases , ring (chemistry) , catalysis , chemistry , medicinal chemistry , combinatorial chemistry , domino , lewis acid catalysis , stereochemistry , organic chemistry
Hard or soft determines the outcome : Five‐membered N,O‐heterocyclic compounds containing an alkyne moiety or a carbonyl group were efficiently synthesized from sulfonamide‐substituted vinylidenecyclopropanediesters, catalyzed by a hard Lewis acid Yb(OTf) 3 and a soft Lewis acid Au I complex, respectively (see scheme). The products were obtained in moderate to excellent yields under mild conditions and the reaction mechanisms were discussed on the basis of control and 18 O‐labeling experiments.