Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 9, Pages 1717-1727Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200901391
Keywords
Asymmetric catalysis; Zinc; Hydroxy amides; Chiral pool; Structure-activity relationships
Categories
Funding
- Ministerio de Educacion y Ciencia of Spain [CTQ2007-67103-002]
- Universidad Complutense de Madrid [PR34/07-15782, 910107]
- Comunidad de Madrid
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Readily accessible, C-2- and pseudo-C-2-symmetric bis(hydroxy amides), derived from commercially available (+)-ketopinic acid and protic diamines, are promising, cheap, chiral ligands for the synthetically valuable, enantioselective addition of organozinc reagents to carbon electrophiles. A series of ligands of this type, having key structural differences, has been synthesized and tested in the enantioselective ethylation of benzaldehydes and (E)-cinnamaldehyde, in order to gain information on the origin of ligand efficiency. The results obtained allow for the definition of a privileged structural pattern for the design of improved cheap ligands and support interesting models proposed for both the acting catalytic species and the controlling transition states. The most efficient ligands proved to be less efficient than commercially available (-)-MIB; nevertheless, an impressive efficiency level was obtained, which should sustain interest in this cheap type of ligands.
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