The chemistry of alkylstrontium halide analogues, Part 2: Barbier-type dialkylation of esters with alkyl halides

European Journal of Organic Chemistry

Volumn , Issue 20, 2005, Pages 4253-4255

  Miyoshi, Norikazu ^a   Matsuo, Tsuyoshi ^a   Wada, Makoto ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Alkylation; Barbier type reaction; Ester; Strontium

Indexed keywords

EID: 27144528797     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500484     Document Type: Article

References (31)

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2. b) W. E. Lindsell, "Beryllium, Magnesium, Calcium, Strontium and Barium", in Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon Press, Oxford, 1995, vol. 1, chapter 3, p. 57, and references cited therein;
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4. and see also "Product Class 5, 6, 7, and 9", in Science of Synthesis, vol. 7, for Beryllium, Magnesium, Calcium and Barium, respectively.
5. For the synthesis of alkylcalcium halide and the reaction using Rieke calcium, see: a) K. Mochida, S. Ogura, T. Yamanishi, Bull. Chem. Soc., Jpn. 1986, 59, 2633;
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8. For the reaction using Rieke barium, see; a) A. Yanagisawa, S. Habaue, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 8955;
9. b) A. Yanagisawa, S. Habaue, K. Yasue, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 6130.
10. B. J. Wakefield, Organomagnesium Methods in Organic Synthesis, Academic Press, UK, 1995.
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15. Recently, in the view of green chemistry, there are many reports on Barbier-type allylation reactions in aqueous media using indium, tin, zinc, bismuth, etc. For a review see: C.-J. Li, Tetrahedron 1996, 52, 5643.
16. H. Tanaka, S. Nakahata, H. Watanabe, J. Zhao, M. Kuroboshi, S. Torii, Inorg. Chim. Acta 1999, 296, 204.
17. As the rate of intermolecular alkylation of esters mediated by samarium diiodide was very slow, several strategies were developed such as an intramolecular reaction, the addition of metal salts. See, for example: a) G. A. Molander, C. R. Harris, J. Am. Chem. Soc. 1995, 117, 3705;
18. b) F. Machrouhi, B. Hamann, J.-L. Namy, K. B. Kagan, Synlett 1996, 633, and references cited therein;
19. c) A. D. Scala, S. Garbacia, F. Helion, M.-I. Lannou, J.-L. Namy, Eur. J. Org. Chem. 2002, 2989.
20. Lindsell et al. reported that alkylstrontium halides reacted with carbonyl compounds to afford the corresponding products in low yields, with the exception of the reaction with benzophenone; a) G. Gowenlock, W. E. Lindsell, B. Singh, J. Organomet. Chem. 1975, 101, C37;
21. b) G. Gowenlock, W. E. Lindsell, B. Singh, J. Chem. Soc., Dalton 1978, 657.
22. a) M. S. Sell, R. D. Rieke, Synth. Commun. 1995, 25, 4107;
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24. (translated from Zh. Org. Khim.);
25. c) L. N. Cherkasov, S. I. Radchenko, Russian J. Org. Chem. 1994, 30, 456
26. (translated from Zh. Org. Khim.) ;
27. d) L. N. Cherkasov, V. N. Cherkasov, Russian J. Org. Chem. 1995, 31, 2 67
28. (translated from Zh. Org. Khim.).
29. a) N. Miyoshi, K. Kamiura, H. Oka, A. Kita, R. Kuwata, D. Ikehara, M. Wada, Bull. Chem. Soc., Jpn. 2004, 77, 341;
30. b) N. Miyoshi, D. Ikehara, T. Kohno, A. Matsui, T. Kohno, M. Wada, Chem. Lett. 2005, 6, 760.
31. The chemical purity of strontium metal is >95%. Strontium metal was cut in liquid paraffin because it reacts vigorously with water.