Synthesis of chiral 1 '-substituted oxazolinylferrocenes as chiral ligands for Pd-catalyzed allylic substitution reactions
SCIE
SCOPUS
- Title
- Synthesis of chiral 1 '-substituted oxazolinylferrocenes as chiral ligands for Pd-catalyzed allylic substitution reactions
- Authors
- Park, J; Quan, Z; Lee, S; Ahn, KH; Cho, CW
- Date Issued
- 1999-07-10
- Publisher
- ELSEVIER SCIENCE SA
- Abstract
- Chiral 1-oxazolinyl-1'-(diphenylphosphino)ferro 4 and 1-oxazolinyl-1'-(phenylthio)ferrocenes 5 were prepared from 1,1'-dibromoferrocene through 1-oxazolinyl-1'-bromoferrocenes 3. The compounds 4 and 5 were employed as chiral ligands in Pd-catalyzed asymmetric allylic substitution reactions. High enantioselectivities (82-99% ee) and high yields (96-99%) were observed in the substitution reactions of 1,3-diphenylprop-2-enyl acetate and dimethyl malonate with the catalysts generated from [(pi-allyl)PdCl](2) and 4, while the use of 5 led to inferior results (20-75% ee and 25-28% yields). H-1-, (13)'C-, and P-31-NMR data are analyzed for the complexes obtained from the reactions of [(eta(3)-allyl)PdCl](2) and [(eta(3)-1,3-diphenylallyl)PdCl](2) with 4a and 4b. (C) 1999 Elsevier Science S,A. All rights reserved.
- Keywords
- 1 ' -substituted oxazolinylferrocenes; N,P ' -chelate; Pd-catalysts; allylic substitution; TRANSITION-METAL COMPLEXES; ASYMMETRIC-SYNTHESIS; DIPHENYLPHOSPHINO(OXAZOLINYL)FERROCENE LIGANDS; LITHIATION; 1,1' -BIS(OXAZOLINYL)FERROCENES; PHOSPHINOARYLOXAZOLINES; ALKYLATION
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/20358
- DOI
- 10.1016/S0022-328X(99)00125-4
- ISSN
- 0022-328X
- Article Type
- Article
- Citation
- JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 584, no. 1, page. 140 - 146, 1999-07-10
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