Several chiral 8-diphenylphosphino-2-oxazolinylquinolines were synthesized starting from 2-cyano-8-hydroxyquinoline. These N,N,P-chelates were successfully employed in the Ru(II)-catalyzed asymmetric cyclopropanation reactions of diazo-alkenes. The catalytic system exhibited good reactivity and high thermal stability and provided high yields in the intramolecular cyclopropanation, albeit somewhat decreased enantioselectivities compared to known catalytic systems. A dramatic dependency of the enantioselectivity on the substituents of the oxazoline ring was observed. (C) 1999 Elsevier Science Ltd. All rights reserved.
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Nagoya Univ, Dept Appl Chem, Chikusa Ku, Grad Sch Engn, Nagoya, Aichi, JapanNagoya Univ, Dept Appl Chem, Chikusa Ku, Grad Sch Engn, Nagoya, Aichi, Japan
Ito, Jun-ichi
Asai, Ryosuke
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Nagoya Univ, Dept Appl Chem, Chikusa Ku, Grad Sch Engn, Nagoya, Aichi, JapanNagoya Univ, Dept Appl Chem, Chikusa Ku, Grad Sch Engn, Nagoya, Aichi, Japan
Asai, Ryosuke
Nishiyama, Hisao
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Nagoya Univ, Dept Appl Chem, Chikusa Ku, Grad Sch Engn, Nagoya, Aichi, JapanNagoya Univ, Dept Appl Chem, Chikusa Ku, Grad Sch Engn, Nagoya, Aichi, Japan
机构:E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China
Wu, XY
Shen, YY
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机构:E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China
Shen, YY
Ma, B
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机构:E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China
Ma, B
Zhou, QL
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E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R ChinaE China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China
Zhou, QL
Chan, ASC
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机构:E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China