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Enantioselective Access to Spirocyclic Sultams by Chiral Cp x –Rhodium(III)‐Catalyzed Annulations
Author(s) -
Pham Manh V.,
Cramer Nicolai
Publication year - 2016
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.201504998
Subject(s) - enantioselective synthesis , annulation , rhodium , cyclopentadienyl complex , chemistry , catalysis , alkyne , stereochemistry , ligand (biochemistry) , combinatorial chemistry , sulfonyl , medicinal chemistry , organic chemistry , receptor , biochemistry , alkyl
Chiral spirocyclic sultams are a valuable compound class in organic and medicinal chemistry. A rapid entry to this structural motif involves a [3+2] annulation of an N ‐sulfonyl ketimine and an alkyne. Although the directing‐group properties of the imino group for C−H activation have been exploited, the developments of related asymmetric variants have remained very challenging. The use of rhodium(III) complexes equipped with a suitable atropchiral cyclopentadienyl ligand, in conjunction with a carboxylic acid additive, enables an enantioselective and high yielding access to such spirocyclic sultams.