Highly catalytic asymmetric addition of deactivated alkyl grignard reagents to aldehydes.
Generally used and highly reactive RMgBr reagents were effectively deactivated by bis[2-(N,N-dimethylamino)ethyl] ether and then were employed in the highly enantioselective addition of Grignard reagents to aldehydes. The reaction was catalyzed by the complex of commercially available (S)-BINOL and Ti(O(i-)Pr)(4) under mild conditions. Compared with the other observed Grignard reagents, alkyl Grignard reagents showed higher enantioselectivity and they achieved >99% ee.
Da
Chao-Shan
CS
Institute of Biochemistry & Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou 730000, China. dachaoshan@lzu.edu.cn
Wang
Jun-Rui
JR
Yin
Xiao-Gang
XG
Fan
Xin-Yuan
XY
Liu
Yi
Y
Yu
Sheng-Li
SL
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005019:Ethyl Ethers / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; C406944:BINOL, naphthol; D005019:Ethyl Ethers; D007202:Indicators and Reagents; D009284:Naphthols; C021151:bis(2-(dimethylamino)ethyl) ether