On-step synthesis of a bifunctional BINOL ligand for the highly enantioselective cyanation of aliphatic aldehydes.
[reaction: see text] An efficient one-step synthesis of the optically active bifunctional BINOL ligand (S)-3 has been developed. It was found that (S)-3 in combination with Me2AlCl is a highly enantioselective catalyst for the addition of TMSCN to aliphatic aldehydes of diverse structures and is also among the most practical ones. A remarkable positive nonlinear effect was found for this chiral ligand.
Qin
Ying-Chuan
YC
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319, USA.
Liu
Lan
L
Pu
Lin
L
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003486:Cyanides / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000447:Aldehydes; C406944:BINOL, naphthol; D003486:Cyanides; D008024:Ligands; D009284:Naphthols; D014297:Trimethylsilyl Compounds; C058010:trimethylsilyl cyanide