Enantioselective Synthesis of Spiroimines by Asymmetric Decarboxylative Alkylation/Isomerization/[3+2]‐Cycloaddition Reaction of Azidoalkenes. Issue 34 (24th October 2014)

• Record Type: Journal Article
• Authors: Rambla, Matt; Duroure, Leslie; Chabaud, Laurent; Guillou, Catherine
• Is Part Of: European journal of organic chemistry. Issue 34(2014)
• Page Start: 7716
• Page End: 7720
• Publication Date: 2014-10-24
• Subjects: Asymmetric synthesis -- Azides -- Cycloaddition -- Palladium -- Spiro compounds; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403161
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The synthesis of chiral spiroimines, one of the pharmacophores of the marine neurotoxin gymnodimine A is described. The approach relies on a three‐step sequence that includes a palladium‐catalyzed asymmetric decarboxylative alkylation, an isomerization and a [3+2]‐cycloaddition reaction of an azidoalkene to build the imine. Abstract : The synthesis of optically active spiroimines, one of the pharmacophores of the marine neurotoxin gymnodimine A, is described. The approach relies on a three‐step sequence that includes a palladium‐catalyzed asymmetric decarboxylative alkylation, an isomerization and a [3+2]‐cycloaddition reaction of an azidoalkene to build the imine.