TY - JOUR
T1 - New bidentate chiral phosphoramidites in copper-catalyzed asymmetric 1,4-addition of diethylzinc to cyclic α,β-enones: Enantioselective tandem 1,4-addition-aldol reactions with 2-cyclopentenone
T2 - enantioselective tandem 1,4-addition-aldol reactions with 2-cyclopentenone
AU - Mandoli, A.
AU - Arnold, L.A.
AU - de Vries, Andreas
AU - Salvadori, P.
AU - Feringa, B.L.
N1 - Relation: http://www.rug.nl/scheikunde/
date_submitted:2005
Rights: University of Groningen. Stratingh Institute
PY - 2001
Y1 - 2001
N2 - New bidentate phosphoramidites were prepared starting from α,α,α',α'-tetraphenyl-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (TADDOL) or 1,1'-bi-2-naphthol (BINOL) and either 1,2-ethylene- or 1,3-propylenediamine N,N'-disubstituted with achiral or chiral groups. The use of these ligands in the copper-catalyzed enantioselective conjugate addition of diethylzinc to 2-cyclohexenone and 2-cyclopentenone afforded products with e.e.s of up to 89 and 83%, respectively.
AB - New bidentate phosphoramidites were prepared starting from α,α,α',α'-tetraphenyl-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (TADDOL) or 1,1'-bi-2-naphthol (BINOL) and either 1,2-ethylene- or 1,3-propylenediamine N,N'-disubstituted with achiral or chiral groups. The use of these ligands in the copper-catalyzed enantioselective conjugate addition of diethylzinc to 2-cyclohexenone and 2-cyclopentenone afforded products with e.e.s of up to 89 and 83%, respectively.
KW - CONJUGATE ADDITION
KW - ORGANOZINC REAGENTS
KW - DIALKYLZINC REAGENTS
KW - LIGANDS
KW - ENONES
KW - COMPLEXES
UR - http://www.scopus.com/inward/record.url?eid=2-s2.0-0035973774&partnerID=40&md5=a9a2db25238f08e9dd733a3a460cf3cf
U2 - 10.1016/S0957-4166(01)00348-2
DO - 10.1016/S0957-4166(01)00348-2
M3 - Article
SN - 0957-4166
VL - 12
SP - 1929
EP - 1937
JO - Tetrahedron-Asymmetry
JF - Tetrahedron-Asymmetry
IS - 13
ER -