TY - JOUR
T1 - Aerobic oxidative kinetic resolution of racemic alcohols with bidentate ligand-binding Ru(salen) complex as catalyst
AU - Nakamura, Yukie
AU - Egami, Hiromichi
AU - Matsumoto, Kazuhiro
AU - Uchida, Tatsuya
AU - Katsuki, Tsutomu
PY - 2007/7/9
Y1 - 2007/7/9
N2 - Chiral Ru(salen)(nitrosyl) complex 1 is a useful catalyst for asymmetric aerobic oxidation of alcohols under photo-irradiation. In this study, it was found that addition of β-hydroxy ketone or 1,3-diketone had a significant influence on its asymmetric catalysis. For example, the addition of 1,3-bis(p-bromophenyl)propane-1,3-dione 9 improved the relative reaction ratio in kinetic resolution of simple racemic secondary alcohols up to 30, while the addition gave an adverse effect on desymmetrization of an acyclic meso-1,3-diol. This additive effect was considered to be attributable to the chelate formation of the β-hydroxy ketone or 1,3-diketone with a Ru(salen) complex.
AB - Chiral Ru(salen)(nitrosyl) complex 1 is a useful catalyst for asymmetric aerobic oxidation of alcohols under photo-irradiation. In this study, it was found that addition of β-hydroxy ketone or 1,3-diketone had a significant influence on its asymmetric catalysis. For example, the addition of 1,3-bis(p-bromophenyl)propane-1,3-dione 9 improved the relative reaction ratio in kinetic resolution of simple racemic secondary alcohols up to 30, while the addition gave an adverse effect on desymmetrization of an acyclic meso-1,3-diol. This additive effect was considered to be attributable to the chelate formation of the β-hydroxy ketone or 1,3-diketone with a Ru(salen) complex.
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U2 - 10.1016/j.tet.2007.03.105
DO - 10.1016/j.tet.2007.03.105
M3 - Article
AN - SCOPUS:34249331348
VL - 63
SP - 6383
EP - 6387
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 28
ER -