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C 1 ‐Symmetric Aminosulfoximines in Copper‐Catalyzed Asymmetric Vinylogous Mukaiyama Aldol Reactions
Author(s) -
Frings Marcus,
Atodiresei Iuliana,
Wang Yutian,
Runsink Jan,
Raabe Gerhard,
Bolm Carsten
Publication year - 2010
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.200903077
Subject(s) - aldol reaction , electrophile , nucleophile , chemistry , catalysis , copper , ligand (biochemistry) , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , receptor
Vinylogous Mukaiyama‐type aldol reactions have been catalyzed by a combination of Cu(OTf) 2 and readily available C 1 ‐symmetric aminosulfoximines. After a fine‐tuning of the reaction conditions and an optimization of the modularly assembled ligand structure, high stereoselectivities and excellent yields have been achieved in catalyzed reactions involving various electrophile/nucleophile combinations. The relative and absolute configurations of two products were assigned by X‐ray single crystal structure analysis and a comparison of calculated and experimental CD spectra.