27727-45-3Relevant articles and documents
Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metal complexes.
Li,Yang,Kozlowski
, p. 1137 - 1140 (2001)
[reaction: see text]. Chiral 1,5-diaza-cis-decalins have been examined as ligands in the enantioselective oxidative biaryl coupling of substituted 2-naphthol derivatives. Under the optimal conditions employing a 1,5-diaza-cis-decalin copper(I) iodide comp
Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metal complexes: Efficient formation of chiral functionalized BINOL derivatives
Li, Xiaolin,Hewgley, J. Brian,Mulrooney, Carol A.,Yang, Jaemoon,Kozlowski, Marisa C.
, p. 5500 - 5511 (2007/10/03)
Chiral 1,5-diaza-cis-decalins have been examined as ligands in the enantioselective oxidative biaryl coupling of substituted 2-naphthol derivatives. Under the optimal conditions employing 2.5-10 mol % of a 1,5-diaza-cis-decalin copper(II) catalyst with oxygen as the oxidant, enantioselective couplings (44-96% ee) could be achieved for a range of 3-substituted 2-naphthols including the ester, ketone, phosphonyl, and sulfonyl derivatives. The relationship between the substitution of the naphthalene starting materials and reactivity/selectivity is determined by several factors which act in concert: (1) the effect of substituents on the oxidation potential of the substrate, (2) the ability of the substrate to participate in a chelated copper complex which depends on (a) the inherent coordinating ability of the 3-substituent and (b) substituent steric interactions that affect chelation between the 2-hydroxyl and 3-substituent, (3) the effect of substituents on dissociation of the product from the copper catalyst.
