Lead Iodide-HMPA as a Novel Catalyst for Chemo- and Diastereoselective Carbonyl Allylation of α,β-Epoxy Ketones with Allylic Stannanes

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 3790-3791

  Shibata, Ikuya ^a   Fukuoka, Shoji ^a   Yoshimura, Naritoshi ^a   Matsuda, Haruo ^a,b   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

^b OSAKA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001523433     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970242q     Document Type: Article

References (18)

1. A recent review: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Pereyre, M.; Quintard J. P; Rahm, A. Tin in Organic Synthesis; Butterworth, London, 1987. (c) Wardell, J. I. In Chemistry of Tin; Harrison, P. G., Ed.; Blackie: Glasgow, 1989; pp 315-358. (d) Omae, I. Organotin Chemistry; Elsevier: Amsterdam, 1989.
2. A recent review: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Pereyre, M.; Quintard J. P; Rahm, A. Tin in Organic Synthesis; Butterworth, London, 1987. (c) Wardell, J. I. In Chemistry of Tin; Harrison, P. G., Ed.; Blackie: Glasgow, 1989; pp 315-358. (d) Omae, I. Organotin Chemistry; Elsevier: Amsterdam, 1989.
3. A recent review: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Pereyre, M.; Quintard J. P; Rahm, A. Tin in Organic Synthesis; Butterworth, London, 1987. (c) Wardell, J. I. In Chemistry of Tin; Harrison, P. G., Ed.; Blackie: Glasgow, 1989; pp 315-358. (d) Omae, I. Organotin Chemistry; Elsevier: Amsterdam, 1989.
4. A recent review: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Pereyre, M.; Quintard J. P; Rahm, A. Tin in Organic Synthesis; Butterworth, London, 1987. (c) Wardell, J. I. In Chemistry of Tin; Harrison, P. G., Ed.; Blackie: Glasgow, 1989; pp 315-358. (d) Omae, I. Organotin Chemistry; Elsevier: Amsterdam, 1989.
5. For example: (a) Keck, G. E.; Castellino, S.; Andrus, M. B. Selectivities in Lewis Acid Promoted Reactions; Kluwer Acad. Pub.: Dordrecht, 1988; p 73. (b) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395. (c) Marshall, J. A. Chem. Rev. 1996, 96, 31. (d) Carey, J. S.; Coulter, T. S.; Hallett, D. J.; Maguire, R. J.; McNeill, A. H.; Stanway, S. J.; Teerawutgulrag, A.; Thomas, E. J. Pure Appl. Chem. 1996, 68, 707.
6. For example: (a) Keck, G. E.; Castellino, S.; Andrus, M. B. Selectivities in Lewis Acid Promoted Reactions; Kluwer Acad. Pub.: Dordrecht, 1988; p 73. (b) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395. (c) Marshall, J. A. Chem. Rev. 1996, 96, 31. (d) Carey, J. S.; Coulter, T. S.; Hallett, D. J.; Maguire, R. J.; McNeill, A. H.; Stanway, S. J.; Teerawutgulrag, A.; Thomas, E. J. Pure Appl. Chem. 1996, 68, 707.
7. For example: (a) Keck, G. E.; Castellino, S.; Andrus, M. B. Selectivities in Lewis Acid Promoted Reactions; Kluwer Acad. Pub.: Dordrecht, 1988; p 73. (b) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395. (c) Marshall, J. A. Chem. Rev. 1996, 96, 31. (d) Carey, J. S.; Coulter, T. S.; Hallett, D. J.; Maguire, R. J.; McNeill, A. H.; Stanway, S. J.; Teerawutgulrag, A.; Thomas, E. J. Pure Appl. Chem. 1996, 68, 707.
8. For example: (a) Keck, G. E.; Castellino, S.; Andrus, M. B. Selectivities in Lewis Acid Promoted Reactions; Kluwer Acad. Pub.: Dordrecht, 1988; p 73. (b) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395. (c) Marshall, J. A. Chem. Rev. 1996, 96, 31. (d) Carey, J. S.; Coulter, T. S.; Hallett, D. J.; Maguire, R. J.; McNeill, A. H.; Stanway, S. J.; Teerawutgulrag, A.; Thomas, E. J. Pure Appl. Chem. 1996, 68, 707.
9. Yano, K.; Baba, A.; Matsuda, H. Bull. Chem, Soc. Jpn. 1992, 65, 66.
10. (a) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 36, 9497.
11. (b) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1996, 61, 105.
12. (c) Yasuda, M.; Miyai, T.; Shibata, I.; Baba, A.; Nomura, R.; Matsuda, H. Tetrahedron Lett. 1995, 36, 9497.
13. 2 (0.1 equiv)-HMPA (0.1 equiv) gave 3a in lower yield (63%).
14. 2O (9:1). Care must be taken in the handling of tin, lead reagents, and HMPA because of their toxity.
15. 2-HMPA caused double allylation at the carbonyl and epoxide groups of 1d, This is because of the nucleophilicity of the Sn-I bond toward epoxide rings. Shibata, I.; Baba, A.; Iwasaki, H., Matsuda, H. J. Org. Chem. 1986, 51, 2177.
16. The structures of crystalline products 3a and 3b were indicated by X-ray analysis. The author has deposited atomic coordinates for 3a,b with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
17. For example: (a) Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323. (b) Smith, J. G. Synthesis 1984, 629.
18. For example: (a) Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323. (b) Smith, J. G. Synthesis 1984, 629.