Organocatalytic Enantioselective Decarboxylative Reaction of Malonic Acid Half Thioesters with Cyclic N‐Sulfonyl Ketimines by Using N‐Heteroarenesulfonyl Cinchona Alkaloid Amides. Issue 10 (22nd January 2015)

• Record Type: Journal Article
• Authors: Nakamura, Shuichi; Sano, Masahide; Toda, Ayaka; Nakane, Daisuke; Masuda, Hideki
• Is Part Of: Chemistry. Volume 21:Issue 10(2015)
• Page Start: 3929
• Page End: 3932
• Publication Date: 2015-01-22
• Subjects: enantioselectivity -- Mannich reaction -- organocatalysis -- quaternary stereocenters; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201406270
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The organocatalytic enantioselective decarboxylative Mannich reaction of malonic acid half thioesters (MAHTs) with cyclic N ‐sulfonyl ketimines by using N ‐heteroarenesulfonyl cinchona alkaloid amides afforded products with high enantioselectivity. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. The reaction proceeds through a nucleophilic addition of the MAHTs to the ketimines prior to decarboxylation. Abstract : Lose to win : The organocatalytic enantioselective decarboxylative Mannich reaction of malonic acid half thioesters (MAHTs) with cyclic ketimines by using N ‐heteroarenesulfonyl cinchona alkaloid amides afforded products with high enantioselectivity (see scheme). Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. The reaction proceeds through a nucleophilic addition of the MAHTs to the ketimines prior to decarboxylation.