TY - JOUR
T1 - New chiral tetraaza ligands for the efficient enantioselective addition of dialkylzinc to aromatic aldehydes
AU - Burguete, M. Isabel
AU - Escorihuela, Jorge
AU - Luis, Santiago V.
AU - Lledós, Agustí
AU - Ujaque, Gregori
N1 - Funding Information:
Financial support from the Spanish Ministerio de Educación y Ciencia (MEC, projects CTQ2005-08016-C03 and CTQ2005-09000-C02-01), Fundació Caixa Castelló-UJI (project P1-1B2004-13), FEDER and Consolider (Ingenio-2010 CSD2007-00006) is acknowledged. J.E. thanks MEC-CSIC for a predoctoral fellowship. G.U. acknowledges ‘Ramon y Cajal’ contract funded by Spanish MEC.
PY - 2008/10/6
Y1 - 2008/10/6
N2 - A series of chiral tetraaza ligands were studied for the enantioselective addition of dialkylzinc to aldehydes. These bis(amino amide) ligands show high enantioselectivity in the addition of organozincs to aromatic aldehydes. Different structural elements on the ligands seem to play an important role in determining the observed enantioselectivity. Ligand 4b (N,N′-bis(N-l-valinyl)-1,3-diaminopropane, with an aliphatic spacer with 3C atoms) catalyzed the addition of Et2Zn to benzaldehyde, 1-naphtaldehyde, 4-methoxybenzaldehyde, and 4-chlorobenzaldehyde to give the corresponding alcohol products with excellent conversions and selectivities and with enantioselectivities of 99, 97, 98, and 82%, respectively. DFT calculations provide an understanding of the mechanism of the enantioselection process.
AB - A series of chiral tetraaza ligands were studied for the enantioselective addition of dialkylzinc to aldehydes. These bis(amino amide) ligands show high enantioselectivity in the addition of organozincs to aromatic aldehydes. Different structural elements on the ligands seem to play an important role in determining the observed enantioselectivity. Ligand 4b (N,N′-bis(N-l-valinyl)-1,3-diaminopropane, with an aliphatic spacer with 3C atoms) catalyzed the addition of Et2Zn to benzaldehyde, 1-naphtaldehyde, 4-methoxybenzaldehyde, and 4-chlorobenzaldehyde to give the corresponding alcohol products with excellent conversions and selectivities and with enantioselectivities of 99, 97, 98, and 82%, respectively. DFT calculations provide an understanding of the mechanism of the enantioselection process.
UR - https://www.scopus.com/pages/publications/49849087775
U2 - 10.1016/j.tet.2008.07.099
DO - 10.1016/j.tet.2008.07.099
M3 - Article
AN - SCOPUS:49849087775
SN - 0040-4020
VL - 64
SP - 9717
EP - 9724
JO - Tetrahedron
JF - Tetrahedron
IS - 41
ER -