Highly Enantioselective Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylide Catalyzed by a Copper(I)/ClickFerrophos Complex

Highly Enantioselective Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylide Catalyzed by a Copper(I)/ClickFerrophos Complex

A copper(I)/ClickFerrophos complex catalyzed the asymmetric 1,3-dipolar cycloaddition reaction of methyl N-benzylideneglycinate (the source of azomethine ylides) with vinyl sulfone to give the exo-2,4,5-trisubstituted pyrrolidine in good yield with high enantioselectivity (99% ee). The complex also...

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Bibliographic Details
Published in:Organic letters Vol. 10; no. 9; pp. 1747 - 1750
Main Authors: Fukuzawa, Shin-ichi, Oki, Hiroshi
Format: Journal Article
Language:English
Published: United States American Chemical Society 01-05-2008
Subjects:
Azo Compounds - chemical synthesis
Azo Compounds - chemistry
Catalysis
Copper - chemistry
Phosphines - chemistry
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
Stereoisomerism
Thiosemicarbazones - chemical synthesis
Thiosemicarbazones - chemistry
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Summary:A copper(I)/ClickFerrophos complex catalyzed the asymmetric 1,3-dipolar cycloaddition reaction of methyl N-benzylideneglycinate (the source of azomethine ylides) with vinyl sulfone to give the exo-2,4,5-trisubstituted pyrrolidine in good yield with high enantioselectivity (99% ee). The complex also effectively catalyzed reactions of other dipolarophiles such as acrylates, maleate, and maleimides to give the exo-2,4,5-, and 2,3,4,5-substituted pyrrolidine derivatives with high diastereo- and enantioselectivities.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol8003996