Organocatalytic Enantioselective Decarboxylative Reaction of Malonic Acid Half Thioesters with Cyclic  N ‐Sulfonyl Ketimines by Using  N ‐Heteroarenesulfonyl Cinchona Alkaloid Amides | Zendy

Nakamura Shuichi | Zendy; Sano Masahide | Zendy; Toda Ayaka | Zendy; Nakane Daisuke | Zendy; Masuda Hideki | Zendy

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Organocatalytic Enantioselective Decarboxylative Reaction of Malonic Acid Half Thioesters with Cyclic N ‐Sulfonyl Ketimines by Using N ‐Heteroarenesulfonyl Cinchona Alkaloid Amides

Author(s) -

Nakamura Shuichi,

Sano Masahide,

Toda Ayaka,

Nakane Daisuke,

Masuda Hideki

Publication year - 2015

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201406270

Subject(s) - enantioselective synthesis , cinchona , chemistry , malonic acid , decarboxylation , sulfonyl , enantiomer , organocatalysis , organic chemistry , cinchona alkaloids , nucleophile , catalysis , alkyl

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.

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