C1-symmetric aminosulfoximines in copper-catalyzed asymmetric vinylogous Mukaiyama aldol reactions.
Vinylogous Mukaiyama-type aldol reactions have been catalyzed by a combination of Cu(OTf)2 and readily available C1-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.
Institut für Organische Chemie der RWTH Aachen University, Landoltweg 1, 52056 Aachen (Germany), Fax: (+49) 241-8092391.
Marcus
M
Frings
Iuliana
I
Atodiresei
Yutian
Y
Wang
Jan
J
Runsink
Gerhard
G
Raabe
Carsten
C
Bolm
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry*
D000447:Aldehydes; D008024:Ligands; D013457:Sulfur Compounds; D003300:Copper; C116609:3-hydroxybutanal
Mukaiyama reaction; aldol reaction; asymmetric catalysis; copper; sulfoximine