Application of beta-hydroxysulfoximines in catalytic asymmetric phenyl transfer reactions for the synthesis of diarylmethanols.
Enantiomerically enriched diarylmethanols have been prepared by catalyzed asymmetric phenyl transfer reactions onto aromatic aldehydes with use of readily available beta-hydroxysulfoximines as catalysts. As the aryl source, combinations of diethylzinc with either diphenylzinc or triphenylborane have been applied affording arylphenylmethanols with up to 93% ee in good yields. Various functionalized aldehydes and heterocyclic substrates are tolerated, yielding synthetically relevant products.
Sedelmeier
Jörg
J
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52056, Aachen, Germany.
Bolm
Carsten
C
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007097:Imines / Q000737:chemistry*; D000432:Methanol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D007097:Imines; D013440:Sulfides; D000432:Methanol