Enantioselective Synthesis of Spiroimines by Asymmetric Decarboxylative Alkylation/Isomerization/[3+2]‐Cycloaddition Reaction of Azidoalkenes | Zendy

Rambla Matt | Zendy; Duroure Leslie | Zendy; Chabaud Laurent | Zendy; Guillou Catherine | Zendy

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Enantioselective Synthesis of Spiroimines by Asymmetric Decarboxylative Alkylation/Isomerization/[3+2]‐Cycloaddition Reaction of Azidoalkenes

Author(s) -

Rambla Matt,

Duroure Leslie,

Chabaud Laurent,

Guillou Catherine

Publication year - 2014

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.201403161

Subject(s) - chemistry , enantioselective synthesis , isomerization , cycloaddition , alkylation , imine , pharmacophore , combinatorial chemistry , stereochemistry , organic chemistry , catalysis

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.

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