Copper-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Imino Esters to Unsaturated Sultones

The asymmetric 1,3-dipolar cycloaddition of glycine imino esters to 1-propene-1,3-sultone or sulfocoumarins is described. The reaction was efficiently catalyzed by Cu-(MeCN)(4)BF4/DTBM-Segphos or Cu(MeCN)(4)BF4/tBu-FcPhox at room temperature to afford fused pyrrolidines as single regioisomers with e...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 85; no. 12; pp. 8142 - 8148
Main Authors Furuya, Shohei, Kanemoto, Kazuya, Fukuzawa, Shin-ichi
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 19.06.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ZH SYSTEMS
POTENTIAL 1,3-DIPOLES
INHIBITORS
MECHANISM
DERIVATIVES
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Summary:The asymmetric 1,3-dipolar cycloaddition of glycine imino esters to 1-propene-1,3-sultone or sulfocoumarins is described. The reaction was efficiently catalyzed by Cu-(MeCN)(4)BF4/DTBM-Segphos or Cu(MeCN)(4)BF4/tBu-FcPhox at room temperature to afford fused pyrrolidines as single regioisomers with excellent diastereoselectivity and enantioselectivity. The broad substrate scope of this reaction provides convenient access to structurally diverse multisubstituted pyrrolidines in an optically pure fashion.
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01023