Rhodium-catalyzed reformatsky-type reaction

Organic Letters

Volumn 2, Issue 16, 2000, Pages 2549-2551

  Kanai, Kazuo ^a   Wakabayashi, Hitoshi ^a   Honda, Toshio ^a  

^a HOSHI UNIVERSITY   (Japan)

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Indexed keywords

EID: 0000825178     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006268c     Document Type: Article

References (33)

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2. (b) Rathke, M. W.; Weipert, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; New York, 1991; Vol. 2, p 277.
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18. 4). and the residue was purified by column chromatography on silica gel.
19. In entry 1, Table 1, the reaction gave 3a in a 32% yield, and unreacted benzaldehyde was recovered (66%) with 1.1 molar equiv of diethylzinc.
20. 3a: Picotin, G.; Miginiac, P. J. Org. Chem. 1987, 52, 4796.
21. 3b: Hart, J. D.; Krishnamurthy, R. J. Org. Chem. 1992, 57, 4457.
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23. 3d: Kiyooka, S.; Shahid, K. A.; Hena, M. A. Tetrahedron Lett. 1999, 40, 6447.
24. 3e: Araki, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988, 18, 453. 3f: See ref 7.
25. 3g: Martin, J.; Pinhey, J. T. Molecules 1998, 3, M59.
26. 3h: Couffignal, R.; Gaudemar, M. J. Organomet. Chem. 1973, 60, 209.
27. 3i: Enholm, E. J.; Jiang, S.; Abboud, K. J. Org. Chem. 1993, 58, 4061
28. , 3j: Conan, A.; Sibille, S.; Perichon, J. J. Org. Chem. 1991, 56, 2018.
29. 3k: Ruano, J. L. G.; Barros, D.; Maestro, M. C: Araya-Maturana, R.; Fischer, J. J. Org. Chem. 1996, 61, 9462.
30. Under the conventional Reformatsky reaction conditions, the syn: anti product ratios are 37:63 for 3b and 67:33 for 3f (refs I and 17).
31. Heathcock, C. H.; In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984: Vol. 3, p 144.
32. Hansen, M. M.; Bartlett, P. A.; Heathcock, C. H. Organometallics 1987, 6, 2069. Palmer and Reid reported the generation of n-propylzinc ester enolate from (-)-menthyl bromoacetate and di-n-propylzine. However, their condition for preparing zinc enolate was relatively vigorous compared to ours developed above, see: Palmer, M. H.; Reid, J. A. J. Chem. Soc. 1962, 1762.
33. Hansen, M. M.; Bartlett, P. A.; Heathcock, C. H. Organometallics 1987, 6, 2069. Palmer and Reid reported the generation of n-propylzinc ester enolate from (-)-menthyl bromoacetate and di-n-propylzine. However, their condition for preparing zinc enolate was relatively vigorous compared to ours developed above, see: Palmer, M. H.; Reid, J. A. J. Chem. Soc. 1962, 1762.