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Volumn 17, Issue 20, 1998, Pages 4374-4379

Synthesis and X-ray crystal structures of palladium(II) and platinum(II) complexes of the PCP-type chiral tridentate ligand (1R,1′R)-1,3-bis[1-(diphenylphosphino)ethyl]benzene. Use in the asymmetric aldol reaction of methyl isocyanoacetate and aldehydes

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EID: 0001286113     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980461h     Document Type: Article
Times cited : (212)

References (54)
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    • For some reports on the asymmetric aldol reaction of isocyanoacetates and aldehydes see: (a) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. (b) Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1987, 28, 6215. (c) Ito, Y.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T. Tetrahedron Lett. 1988, 29, 235. (d) Ito, Y.; Sawamura, M.; Kobayashi, M.; Hayashi, T. Tetrahedron Lett. 1988, 29, 6321. (e) Ito, Y.; Sawamura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681. (f) Togni, A.; Pastor, S. D. J. Org. Chem. 1990, 55, 1649. (g) Hayashi, T.; Sawamura, M.; Ito, Y. Tetrahedron 1992, 48, 1999. (h) Nesper, R.; Pregosin, P. S.; Puntener, K.; Worle, M. Helv. Chim. Acta 1993, 76, 2239. (i) Soloshonok, V. A.; Hayashi, T. Tetrahedron Lett. 1994, 35, 2713. (j) Soloshonok, V. A.; Hayashi, T. Tetrahedron: Asymmetry 1994, 5, 1091. (k) Soloshonok, V. A.; Kacharov, A. D.; Hayashi, T. Tetrahedron 1996, 52, 245.
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    • note
    • 1H NMR showed the reaction proceeded very cleanly and nearly quantitatively to the desired products.
  • 49
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    • note
    • Absolute configuration was determined by separating the trans and cis isomers by silica gel chromatography and comparing the optical rotations with those previously reported. See ref 17a.
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    • Frenz, B. A. The Enraf-Nonius CAD4 SDP-A Real-time System for Concurrent X-Ray Data Collection and Crystal Structure Determination. In Computing in Crystallography; Schenk, H., Olthof-Hazelkamp, R., vanKonigsveld, H., Bassi, G. C., Eds.; Delft University Press: Delft, Holland, 1978; pp 64-71.
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