SmI2-Induced 2,3-Wittig Rearrangement: Regioselective Generation of α-Allyloxy Carbanions via 1,5-Hydrogen Transfer of Vinyl Radicals

Journal of Organic Chemistry

Volumn 62, Issue 22, 1997, Pages 7542-7543

  Kunishima, Munetaka ^a   Hioki, Kazuhito ^a   Kono, Kazuhiro ^a   Kato, Akira ^b   Tani, Shohei ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

^b NIIGATA UNIVERSITY OF PHARMACY AND APPLIED LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000095069     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9714223     Document Type: Article

References (35)

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2. For reviews on 2,3-Wittig rearrangement, see: (a) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885-902. (b) Marshall, J. A. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 975-1014. (c) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105-210.
3. For reviews on 2,3-Wittig rearrangement, see: (a) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885-902. (b) Marshall, J. A. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 975-1014. (c) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105-210.
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5. For recent reports, see: (a) Konno, T.; Umetani, H.; Kitazume, T. J. Org. Chem. 1997, 119, 137-150. (b) Nakai, T.; Tomooka, K. Pure Appl. Chem. 1997, 69, 595-600. (c) Kress, M. H.; Yang, C.; Yasuda, N.; Grabowski, E. Tetrahedron Lett. 1997, 38, 2633-2636.
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18. 3 solution and extracted with ether. The crude product was purified by TLC (hexane:AcOEt = 8:2) to give 20.2 mg of 3-methyl-l-phenyl-3-buten-1-ol (2, 81%) and the hydrodeiodinated allyl ether (1c: X = H, 2.9 mg, 12%).
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21. 9b
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24. This result indicates that the reaction proceeds by 2,3-rearrangement, not by 1,2-rearrangement.
25. A similar result was obtained for the reaction under conditions C.
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31. In the case of (E)- or (Z)-3-iodocrotyl 2-butynyl ether, the threo-selectivity was improved to 84:16, 90:10, respectively.
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34. There are so many methods available for the synthesis of alkenyl halides, see: Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations; VCH: New York, 1989.
35. 1