Ru(II)-catalyzed asymmetric cyclopropanation using chiral diphenylphosphino(oxazolinyl)quinoline ligands

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 hi...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1999-05, Vol.10 (10), p.1903-1911
Main Authors: Park, Sang-Wook, Son, Jeong-Ho, Kim, Sung-Gon, Ahn, Kyo Han
Format: Article
Language:English
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Summary: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.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(99)00190-1