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

• Published in: European journal of organic chemistry Vol. 2019; no. 28; pp. 4561 - 4565
• Main Authors: Furuya, Shohei, Kato, Shuma, Kanemoto, Kazuya, Fukuzawa, Shin‐ichi
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 31.07.2019; Wiley Subscription Services, Inc
• Subjects: Azomethine ylides; Chemical reactions; Chemistry; Chemistry, Organic; Coordination compounds; Copper; Copper compounds; Cycloaddition; Enantiomers; Esters; Glycine; Nitrogen heterocycles; Physical Sciences; Science & Technology; Stereoselectivity; Sulfur heterocycles; Synthetic methods; ZH SYSTEMS; Cycloaddition; Sulfur heterocycles; Nitrogen heterocycles; NITRILE OXIDES; Synthetic methods; POTENTIAL 1,3-DIPOLES; Azomethine ylides; DERIVATIVES
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201900738

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.