Catalytic asymmetric aldol reactions of enolizable carbon pronucleophiles with formaldehyde and ethyl glyoxylate

Advanced Synthesis and Catalysis

Volumn 349, Issue 4-5, 2007, Pages 509-512

  Fukuchi, Isao ^a   Hamashima, Yoshitaka ^a,b   Sodeoka, Mikiko ^a,b  

^a TOHOKU UNIVERSITY   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Aldol reactions; Asymmetric catalysis; Formaldehyde; Glyoxylates; Palladium; Platinum

Indexed keywords

EID: 34547210299     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600568     Document Type: Article

References (28)

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22. 2O and water (19/1). The catalyst was almost insoluble.
23. The Pt complex tested in this paper was prepared according to the procedure for the synthesis of 1, see: A. Fujii, E. Hagiwara, M. Sodeoka, J. Am. Chem. Soc. 1999, 121, 5450-5458. The exact structure of the complex 2a has not yet been confirmed by X-ray analysis.
24. M. Watanabe, S. Kuwahara, N. Harada, M. Koizumi, T. Ohkuma, Tetrahedron: Asymmetry 1999, 10, 2075-2078.
25. Crystallographic data for the structure of 8 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 624275. These data can be obtained online free of charge [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44)-1223-336-003, or mail to: deposit@ccdc.cam.ac.uk].
26. Unfortunately, the enantiomers of other diastereomer were inseparable on chiral HPLC.
27. The reaction of 10 with paraformaldehyde was unsuccessful because of the facile formation of Pd black.
28. We cannot rule out the possibility that the Pd complexes activated ethyl glyoxylate and the enol tautomer of the ketones reacted.