6533b839fe1ef96bd12a6e61

RESEARCH PRODUCT

Organocatalyticanti-Selective Mannich Reactions with Fluorinated Aldimines: Synthesis ofanti-γ-Fluoroalkyl-γ-amino Alcohols

Fatemeh MojarradMaria Dolores Perez CarrionJose Luis AcenaJuan F. Sanz-cerveraSantos Fustero

subject

chemistry.chemical_classificationAldimineTrimethylsilylOrganic ChemistryEnantioselective synthesisEtherAldehydeChemical synthesischemistry.chemical_compoundchemistryOrganocatalysisOrganic chemistryPhysical and Theoretical ChemistryMannich reaction

description

The asymmetric Mannich reaction between fluoroalkyl aldimines and aldehydes catalyzed by α,α-diphenylprolinol trimethylsilyl ether is reported. The corresponding Mannich adducts were reduced in situ to afford anti-β-alkyl-γ-fluoroalkyl-γ-amino alcohols in moderate yields and with very high diastereo- and enantioselectivities. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

https://doi.org/10.1002/ejoc.200900509