Copper‐Catalyzed Regio‐ and Diastereoselective 1,3‐Dipolar Cycloaddition Reactions of Glycine Imino Esters with 1‐Propene‐1,3‐sultone

The 1,3‐dipolar cycloaddition of glycine imino esters (azomethine ylide precursors) with 1‐propene‐1,3‐sultone proceeded smoothly by using copper phosphine complexes at room temperature to give the bicyclic sultone‐fused pyrrolidines as single regio‐ and stereoisomers in good yields. A preliminary a...

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Bibliographic Details
Published in:European journal of organic chemistry 2019-07, Vol.2019 (28), p.4561-4565
Main Authors: Furuya, Shohei, Kato, Shuma, Kanemoto, Kazuya, Fukuzawa, Shin‐ichi
Format: Article
Language:English
Subjects:
Azomethine ylides
Chemical reactions
Coordination compounds
Copper
Copper compounds
Cycloaddition
Enantiomers
Esters
Glycine
Nitrogen heterocycles
Stereoselectivity
Sulfur heterocycles
Synthetic methods
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Summary:The 1,3‐dipolar cycloaddition of glycine imino esters (azomethine ylide precursors) with 1‐propene‐1,3‐sultone proceeded smoothly by using copper phosphine complexes at room temperature to give the bicyclic sultone‐fused pyrrolidines as single regio‐ and stereoisomers in good yields. A preliminary asymmetric reaction with a chiral copper complex gave the fused sultone‐pyrrolidine with excellent enantioselectivity. The copper phosphine complex catalyzed 1,3‐dipolar cycloaddition of glycine imino esters with 1‐propene‐1,3‐sultone proceeded smoothly to give the bicyclic sultone‐fused pyrrolidine as single regio‐ and stereoisomers in good yields. A preliminary asymmetric reaction with a chiral copper complex gave the fused sultone‐pyrrolidine with excellent enantioselectivity.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900738