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Highly Catalytic Asymmetric Addition of Deactivated Alkyl Grignard Reagents to Aldehydes

Chao-Shan Da*, Jun-Rui Wang, Xiao-Gang Yin, Xin-Yuan Fan, Yi Liu and Sheng-Li Yu

*Institute of Biochemistry & Molecular Biology, School of Life Sciences, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China, Email: dachaoshanlzu.edu.cn

C.-S. Da, J.-R. Wang, X.-G. Yin, X.-Y. Fan, Y. Liu, S.-L. Yu, Org. Lett., 2009, 11, 5578-5581.

DOI: 10.1021/ol9020942 (free Supporting Information)


Abstract

Highly reactive RMgBr reagents were effectively deactivated by bis[2-(N,N-dimethylamino)ethyl] ether. These chelated Grignard reagents were employed in a highly enantioselective addition to aldehydes catalyzed by a complex of commercially available (S)-BINOL and Ti(Oi-Pr)4 under mild conditions.

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Key Words

1,2-Addition, Grignard Reaction


ID: J54-Y2009-3580