Direct asymmetric catalytic 1,2-addition of RZnX to aldehydes promoted by AlMe3 and reversal of expected stereochemistry.
Addition of AlMe3 to commercial THF solutions of RZnX (R = aryl, functionalised aryl, vinyl; X = Br, I) simultaneously promotes Schlenk equilibria (leading to competent nucleophiles) and the formation of an Al-Zn-ligand catalyst delivering 80-90% ee for Ar(1)CH(OH)Ar(2) formation from aldehydes.
Shannon
Jonathan
J
School of Chemistry, The University of Nottingham, Nottingham, UKNG7 2RD.
Bernier
David
D
Rawson
Daniel
D
Woodward
Simon
S
D000447:Aldehydes / Q000737:chemistry*; D000535:Aluminum / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D007454:Iodides / Q000737:chemistry; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D017967:Zinc Compounds / Q000737:chemistry*
D000447:Aldehydes; D001965:Bromides; D007454:Iodides; D009942:Organometallic Compounds; D017967:Zinc Compounds; D000535:Aluminum