Magnesium Bromide Mediated Highly Diastereoselective Heterogeneous Hydrogenation of Olefins

Organic Letters

Volumn 4, Issue 8, 2002, Pages 1347-1350

  Bouzide, Abderrahim ^a,b  

^a INRS INSTITUT ARMAND FRAPPIER   (Canada)

^b Invenux Inc   (United States)

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ARTICLE;

EID: 0013297136     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020032m     Document Type: Article

References (41)

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19. 2.
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21. 3) δ 1.02 (d, 7.3 H, 3H), 2.96 (m, 1H), 3.74 (s, 3H), 4.75 (d, J = 8.8 Hz, 1H), 7.27-7.37 (m, 5H).
22. 2 and the use of excess (3-5 equiv) is essential to achieve acceptable selectivity. See: Ward, D. E.; Hrapchak, M. J.; Sales, M. Org. Lett. 2000, 2, 57-60. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10466.
23. 2 and the use of excess (3-5 equiv) is essential to achieve acceptable selectivity. See: Ward, D. E.; Hrapchak, M. J.; Sales, M. Org. Lett. 2000, 2, 57-60. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10466.
24. 3) δ 3.89 (s, 3H), 4.49 (s, 3H), 7.40-7.50 (m, 3H), 7.56 (d, J = 7.5 Hz, 2H), 7.89 (s, 1H).
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28. 2, see: Basaviah, D.; Pandiaraju, S.; Padmaja, K. Synlett 1996, 4, 393-395.
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37. For the synthesis of enantiomerically enriched Baylis-Hillman adducts, see; (a) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219-10220. (b) Iwabuchi, Y.; Sugihara, T.; Esumi, T.; Hatakeyama, S. Tetrahedron Lett. 2001, 42, 7867-7871. (c) Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317-4318. (d) Burgess, K.; Jennings, L. D. J. Org. Chem. 1990, 55, 1138-1139.
38. For the synthesis of enantiomerically enriched Baylis-Hillman adducts, see; (a) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219-10220. (b) Iwabuchi, Y.; Sugihara, T.; Esumi, T.; Hatakeyama, S. Tetrahedron Lett. 2001, 42, 7867-7871. (c) Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317-4318. (d) Burgess, K.; Jennings, L. D. J. Org. Chem. 1990, 55, 1138-1139.
39. For the synthesis of enantiomerically enriched Baylis-Hillman adducts, see; (a) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219-10220. (b) Iwabuchi, Y.; Sugihara, T.; Esumi, T.; Hatakeyama, S. Tetrahedron Lett. 2001, 42, 7867-7871. (c) Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317-4318. (d) Burgess, K.; Jennings, L. D. J. Org. Chem. 1990, 55, 1138-1139.
40. For the synthesis of enantiomerically enriched Baylis-Hillman adducts, see; (a) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219-10220. (b) Iwabuchi, Y.; Sugihara, T.; Esumi, T.; Hatakeyama, S. Tetrahedron Lett. 2001, 42, 7867-7871. (c) Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317-4318. (d) Burgess, K.; Jennings, L. D. J. Org. Chem. 1990, 55, 1138-1139.
41. For a recent diastereoselective heterogeneous hydrogenation of imines, see; Huffman, M. A.; Reider, P. J. Tetrahedron Lett. 1999, 40, 831-834.