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

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 t...

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Published inChinese journal of chemistry Vol. 30; no. 11; pp. 2714 - 2720
Main Author 严定策 李清华 王春江
Format Journal Article
LanguageEnglish
Published Shanghai Wiley Subscription Services, Inc 01.11.2012
Subjects
不对称
偶极环加成反应
催化体系
叶立德
吡咯烷
含氟
甲亚胺
简便
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ISSN1001-604X
1614-7065

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Summary: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.
Bibliography:31-1547/O6
asymmetric catalysis, 1,3-dipolar cycloaddition, azomethine ylide, methyl a-fluoroacrylate, pyrrolidine
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.
Yan, Dingcea Li, Qinghu Wang, Chunjiang College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, China b State Key Laboratory of Organometallie Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 230032, China
ObjectType-Article-1
SourceType-Scholarly Journals-1
content type line 14
ISSN:1001-604X
1614-7065