Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 9, Pages 1696-1705Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201579
Keywords
Asymmetric catalysis; C-C coupling; Michael addition; Lanthanum; Enones
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Funding
- Ministerio de Ciencia e Innovacion (MICINN)
- Fundo Europeu de Desenvolvimento Regional (FEDER) [CTQ2009-13083]
- Generalitat Valenciana [ACOMP/2012/212, ISIC 2012/001]
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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 nitro-alkanes 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.
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