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.
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.
Gui
G
Lu
Fuk Yee
FY
Kwong
Ji-Wu
JW
Ruan
Yue-Ming
YM
Li
Albert S C
AS
Chan
D000447:Aldehydes / Q000737:chemistry*; D000605:Amino Alcohols; D002384:Catalysis; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D000447:Aldehydes; D000605:Amino Alcohols; D015032:Zinc