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Copper‐Catalyzed Regio‐ and Diastereoselective 1,3‐Dipolar Cycloaddition Reactions of Glycine Imino Esters with 1‐Propene‐1,3‐sultone
Author(s) -
Furuya Shohei,
Kato Shuma,
Kanemoto Kazuya,
Fukuzawa Shinichi
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900738
Subject(s) - chemistry , cycloaddition , propene , pyrrolidine , azomethine ylide , 1,3 dipolar cycloaddition , medicinal chemistry , regioselectivity , copper , phosphine , bicyclic molecule , catalysis , stereochemistry , organic chemistry
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.