Cobalt-Mediated Diastereoselective Cross-Coupling Reactions between Cyclic Halohydrins and Arylmagnesium Reagents

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• 作者：Jeffrey M. Hammann ; Andreas K. Steib ; Paul Knochel
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：December 19, 2014
• 年：2014
• 卷：16
• 期：24
• 页码：6500-6503
• 全文大小：377K
• ISSN：1523-7052

文摘

Cyclic TBS-protected iodohydrins (and bromohydrins) undergo a highly diastereoselective cross-coupling with various aryl- and heteroarylmagnesium reagents in the presence of THF-soluble CoCl₂路2LiCl and TMEDA as a ligand leading to trans-2-arylcyclohexanol derivatives in good yields and dr up to >99:1. A range of functional groups are tolerated in the Grignard reagent (e.g., COOR, CN, CF₃, SF₅). The use of heterocyclic iodohydrins leads to trans-3,4-disubstituted pyrrolidines and tetrahydrofurans.