title: Highly catalytic asymmetric addition of deactivated alkyl grignard reagents to aldehydes.
abstract: 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.
authors.affiliation: Institute of Biochemistry & Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou 730000, China. dachaoshan@lzu.edu.cn
authors.forename: Chao-Shan
authors.initials: CS
authors.lastname: Da
authors.forename: Jun-Rui
authors.initials: JR
authors.lastname: Wang
authors.forename: Xiao-Gang
authors.initials: XG
authors.lastname: Yin
authors.forename: Xin-Yuan
authors.initials: XY
authors.lastname: Fan
authors.forename: Yi
authors.initials: Y
authors.lastname: Liu
authors.forename: Sheng-Li
authors.initials: SL
authors.lastname: Yu
mesh_terms: 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
chemical_list: D000447:Aldehydes; C406944:BINOL, naphthol; D005019:Ethyl Ethers; D007202:Indicators and Reagents; D009284:Naphthols; C021151:bis(2-(dimethylamino)ethyl) ether