Iridium-catalyzed enantioselective allylic substitutions with aliphatic nitro compounds as prenucleophiles

Enantioselective Ir-catalyzed allylic alkylations with nitroalkanes and ethyl nitroacetate as nucleophiles are reported. Up to 99% ee was achieved using catalysts prepared by in situ activation of mixtures of phosphorus amidites and [Ir(COD)Cl](2). The method was applied to a synthesis of the antide...

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Bibliographic Details
Published inSynlett no. 5; pp. 697 - 700
Main Authors Dahnz, A, Helmchen, G
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 17.03.2006
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC-SYNTHESIS
CARBONATES
COMPLEXES
catalysis
ETHERIFICATION
ALKYLATIONS
PHOSPHORAMIDITE LIGAND
ring-closing metathesis
iridium
AMINATION
ESTERS
allylic substitution
nitroalkanes
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Summary:Enantioselective Ir-catalyzed allylic alkylations with nitroalkanes and ethyl nitroacetate as nucleophiles are reported. Up to 99% ee was achieved using catalysts prepared by in situ activation of mixtures of phosphorus amidites and [Ir(COD)Cl](2). The method was applied to a synthesis of the antidepressant (1S,2R)-trans-2-phenylcyclopentanamine.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2006-933121