Highly enantioselective addition of in situ prepared arylzinc to aldehydes catalyzed by a series of atropisomeric binaphthyl-derived amino alcohols.
The direct addition of in situ prepared arylzinc to aldehydes with chiral binaphthyl-derived amino alcohols as catalysts can afford optically active diarylmethanols in high yields and with excellent enantioselectivities (up to 99 % ee, ee = enantiomeric excess). By using a single catalyst, both enantiomers of many pharmaceutically interesting diarylmethanols can be obtained by the proper combination of various arylzinc reagents with different aldehydes; this catalytic system also works well for the phenylation of aliphatic aldehydes to give up to 96 % ee.
Lu
Gui
G
Open Laboratory of Chirotechnology of the Institute of Molecular, Technology for Drug Discovery and Synthesis State Key Laboratory of Chinese Medicine and Molecular Pharmacology (Shenzhen), Kowloon, Hong Kong, China.
Kwong
Fuk Yee
FY
Ruan
Ji-Wu
JW
Li
Yue-Ming
YM
Chan
Albert S C
AS
D000447:Aldehydes / Q000737:chemistry*; D000605:Amino Alcohols; D002384:Catalysis; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D000447:Aldehydes; D000605:Amino Alcohols; D015032:Zinc