Homoallyl-substituted vinylcyclopropanes from α,β-unsaturated ketones and allylindium derivatives

Angewandte Chemie - International Edition

Volumn 37, Issue 11, 1998, Pages 1545-1547

  Höppe, Henning A ^a   Lloyd Jones, Guy C ^a   Murray, Martin ^a   Peakman, Torren M ^a   Walsh, Kenneth E ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Allyl complexes; Cyclopropanes; Indium; Ketones; Rearrangements

Indexed keywords

EID: 0343516910     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980619)37:11<1545::AID-ANIE1545>3.0.CO;2-3     Document Type: Article

References (21)

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3. See, for example, a) R. D. Rieke, I.-C. Chao, J. Org. Chem. 1975, 40, 2253-2255; b) M. J. S. Gynane, I. J. Worrall, J. Organometal. Chem. 1974, 81, 329-334.
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7. Reviews: a) C.-J. Li, Tetrahedron 1996, 52, 5643-5668; b) C.-J. Li, Chem. Rev. 1993, 93, 2023-2035; see also c) M. B. Isaac, L. A. Paquette, J. Org. Chem. 1997, 62, 5333-5338, and references therein; indium-induced rearrangements: d) S. Araki, Y. Butsugan, J. Chem. Soc. Chem. Commun. 1989, 1286-1287; e) S. Araki, Y. Butsugan, Bull. Chem. Soc. Jpn. 1991, 64, 727-729; f) J. X. Haberman, C.-J. Li, Tetrahedron Lett. 1997, 38, 4735-4736.
8. Reviews: a) C.-J. Li, Tetrahedron 1996, 52, 5643-5668; b) C.-J. Li, Chem. Rev. 1993, 93, 2023-2035; see also c) M. B. Isaac, L. A. Paquette, J. Org. Chem. 1997, 62, 5333-5338, and references therein; indium-induced rearrangements: d) S. Araki, Y. Butsugan, J. Chem. Soc. Chem. Commun. 1989, 1286-1287; e) S. Araki, Y. Butsugan, Bull. Chem. Soc. Jpn. 1991, 64, 727-729; f) J. X. Haberman, C.-J. Li, Tetrahedron Lett. 1997, 38, 4735-4736.
9. Reviews: a) C.-J. Li, Tetrahedron 1996, 52, 5643-5668; b) C.-J. Li, Chem. Rev. 1993, 93, 2023-2035; see also c) M. B. Isaac, L. A. Paquette, J. Org. Chem. 1997, 62, 5333-5338, and references therein; indium-induced rearrangements: d) S. Araki, Y. Butsugan, J. Chem. Soc. Chem. Commun. 1989, 1286-1287; e) S. Araki, Y. Butsugan, Bull. Chem. Soc. Jpn. 1991, 64, 727-729; f) J. X. Haberman, C.-J. Li, Tetrahedron Lett. 1997, 38, 4735-4736.
10. Reviews: a) C.-J. Li, Tetrahedron 1996, 52, 5643-5668; b) C.-J. Li, Chem. Rev. 1993, 93, 2023-2035; see also c) M. B. Isaac, L. A. Paquette, J. Org. Chem. 1997, 62, 5333-5338, and references therein; indium-induced rearrangements: d) S. Araki, Y. Butsugan, J. Chem. Soc. Chem. Commun. 1989, 1286-1287; e) S. Araki, Y. Butsugan, Bull. Chem. Soc. Jpn. 1991, 64, 727-729; f) J. X. Haberman, C.-J. Li, Tetrahedron Lett. 1997, 38, 4735-4736.
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13. a) S. Araki, T. Shimizu, P. S. Johar, S.-J. Jin, Y. Butsugan, J. Org. Chem. 1991, 56, 2538-2542;
14. b) S. Araki, H. Ito, Y. Butsugan, ibid. 1988, 53, 1833-1835;
15. c) S. Araki, T. Shimizu, S.-J. Jin, Y. Butsugan, J. Chem. Soc. Perkin Trans I 1995, 549-552;
16. d) M. T. Reetz, H. Haning, J. Organometall. Chem. 1997, 541, 117-120 and references therein.
17. CC coupling confirmed the structure of 7a. Complete analytical data for 7b, 7c, 14, and 15 will be reported elsewhere; the diastereomer ratios of 7b, 7c. and 15 were 1:1, 2:1, and 4:1. Analyses of the reaction mixtures by thin-layer chromatography indicated no traces of starting materials 5a-c, 12, or 13. Lower yields for 7c and 15 presumably reflect loss of material through polymerization or formation of highly polar materials.
18. 1H NMR spectrum that revealed no trace of 9a.
19. Vanadium-mediated deoxygenative allylation of allylic alkoxides: a) Y. Kataoka, I. Makihira, H. Akiyama, K. Tani, Tetrahedron 1997, 53, 9525-9540. A catalytic effect of oxygen is noted for this and related processes: b) J. Org. Chem. 1997, 62, 8109-8113.
20. Vanadium-mediated deoxygenative allylation of allylic alkoxides: a) Y. Kataoka, I. Makihira, H. Akiyama, K. Tani, Tetrahedron 1997, 53, 9525-9540. A catalytic effect of oxygen is noted for this and related processes: b) J. Org. Chem. 1997, 62, 8109-8113.
21. S. M. Capps, G. C. Lloyd-Jones, M. Murray, T. M. Peakman, K. E. Walsh, Tetrahedron Lett. 1998, 39, 2853-2856.