6533b853fe1ef96bd12ad378

RESEARCH PRODUCT

Enantioselective LaIII-pyBOX-Catalyzed Nitro-Michael Addition to (E)-2-Azachalcones

Gonzalo BlayM. Carmen MuñozJosé R. PedroCelia Incerti

subject

chemistry.chemical_compoundchemistryLigandStereochemistryOrganic ChemistryNitroEnantioselective synthesisMichael reactionSubstituentOxazolinePhysical and Theoretical ChemistryEnantiomerEnantiomeric excess

description

A [La(OTf)3] complex with a new pyBOX ligand bearing a bulky 1-naphthylmethyl substituent at the 4′-position of the oxazoline ring catalyzes the conjugate addition of nitroalkanes to a broad range of (E)-2-azachalcones, providing the expected nitro-Michael products with good yields and enantiomeric excesses up to 87 %. The optical purity of the products can be increased by a single crystallization. A plausible stereochemical model to account for the observed stereochemistry has been proposed.

yearjournalcountryeditionlanguage
2013-02-06European Journal of Organic Chemistry
https://doi.org/10.1002/ejoc.201201579