Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 6383-6387 |
| Number of pages | 5 |
| Journal | Tetrahedron |
| Volume | 63 |
| Issue number | 28 |
| DOIs | |
| Publication status | Published - Jul 9 2007 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
Aerobic oxidative kinetic resolution of racemic alcohols with bidentate ligand-binding Ru(salen) complex as catalyst. / Nakamura, Yukie; Egami, Hiromichi; Matsumoto, Kazuhiro; Uchida, Tatsuya; Katsuki, Tsutomu.
In: Tetrahedron, Vol. 63, No. 28, 09.07.2007, p. 6383-6387.Research output: Contribution to journal › Article
}
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.
UR - http://www.scopus.com/inward/record.url?scp=34249331348&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=34249331348&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2007.03.105
DO - 10.1016/j.tet.2007.03.105
M3 - Article
VL - 63
SP - 6383
EP - 6387
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 28
ER -