A Facile Access to Fluorinated Pyrrolidines via Catalytic Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides with Methyl a-Fluoroacrylate  

作　　者：严定策 李清华 王春江 

机构地区：[1]College of Chemistry and Molecular Sciences,Wuhan University,Wuhan,Hubei 430072,China [2]State Key Laboratory of Organometallie Chemistry,Shanghai Institute of Organic Chemistry,Shanghai 230032,China

出　　处：《Chinese Journal of Chemistry》2012年第11期2714-2720,共7页中国化学（英文版）

摘　　要：Asymmetric 1,3-dipolar cycloaddition of methyl a-fluoroacrylate with azomethine ylides for the construction of optically active fluorinated pyrrolidines bearing one unique fluorinated quaternary and two tertiary stereogenic cen- ters has been achieved with Cu（CH3CN）4BF4/TF-BiphamPhos complexes for the first time. This catalytic system performs well over a broad scope of substrates, providing the synthetically useful adducts in good yields and excel- lent diastereoselectivities and good to high enantioselectivities.Asymmetric 1,3-dipolar cycloaddition of methyl a-fluoroacrylate with azomethine ylides for the construction of optically active fluorinated pyrrolidines bearing one unique fluorinated quaternary and two tertiary stereogenic cen- ters has been achieved with Cu（CH3CN）4BF4/TF-BiphamPhos complexes for the first time. This catalytic system performs well over a broad scope of substrates, providing the synthetically useful adducts in good yields and excel- lent diastereoselectivities and good to high enantioselectivities.

关 键 词：asymmetric catalysis 1 3-dipolar cycloaddition azomethine ylide methyl a-fluoroacrylate PYRROLIDINE 

分 类 号：TQ252.1[化学工程—有机化工] TQ333.2