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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
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.