[2,3]-Wittig rearrangement initiated by 1,5-hydrogen atom transfer from an o-iodophenyl group on the α-carbon of allylic ethers by reduction with SmI2

Chemistry Letters

Volumn , Issue 7, 1999, Pages 683-684

  Kunishima, Munetaka ^a   Hioki, Kazuhito ^a   Nakata, Daisuke ^a   Nogawa, Shigenobu ^a   Tani, Shohei ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

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EID: 0033473966     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.683     Document Type: Article

References (21)

1. a) M. Kunishima, D. Nakata, C. Goto, K. Hioki, and S. Tani, Synlett, 1998, 1366.
2. b) K. Hioki, K. Kono, S. Tani, and M. Kunishima, Tetrahedron Lett., 39, 5229 (1998).
3. c) M. Kunishima, K. Hioki, K. Kono, A. Kato, and S. Tani, J. Org. Chem., 62, 7542 (1997).
4. 2 under ultrasonic irradiation, followed by addition of a vinyl Grignard reagent afforded secondary allyl alcohols, which then are coupled with an alkyl halide giving 1 a-f.
5. 2, sec: a) M. Murakami, M. Hayashi, and Y. Ito, J. Org. Chem., 57, 793 (1992).
6. b) L. Capella, P. C. Montevecchi, and M. L. Navacchia, J. Org. Chem., 60, 7424 (1995).
7. J. Inanaga, M. Ishikawa, and M. Yamaguchi, Chem. Lett., 1987, 1485.
8. a) M. Kunishima, K. Hioki, T. Ohara, and S. Tani, J. Chem. Soc., Chem. Commun., 1992, 219.
9. b) M. Kunishima, K. Hioki, K. Kono, T. Sakuma, and S. Tani, Chem. Pharm. Bull., 42, 2190 (1994).
10. J. C. Gilbert and B. K. Blackburn, J. Org. Chem., 51, 3656 (1986).
11. 2 we employed was 3.
12. 3 and extracted with ether. The residue was purified by column chromatography (hexane : AcOEt = 85 : 15) to give 2a (20.0 mg, 0.089 mmol) as colorless crystals.
13. The preference for the E-isomer is known as the general trend in [2,3]-Wittig rearrangement, see ref. 10.
14. For reviews on [2,3]-Wittig rearrangement, see: a) T. Nakai and K. Mikami, Chem. Rev., 86, 885 (1986).
15. b) K. Mikami and T. Nakai, Synthesis, 1991, 594.
16. c) R. Brückner, "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 4, p. 873.
17. d) T. Nakai and K. Mikami, Org. React., 46, 105 (1994).
18. The regioselectivity of crotyl 1 -methylallyl ether, of which one allyl group has an α-, and the other has a γ-substituent, by base-deprotonalion was reported to be low (α/γ = 1 : 2), see: T. Nakai, K. Mikami, S. Taya, and Y. Fujita, J. Am. Chem. Soc., 103, 6492 (1981).
19. For reviews on [1,2]-Witig rearrangement, see: a) U. Schöllkopf, Angew. Chem., Int. Ed. Engl., 9, 763 (1970).
20. b) J. A. Marshall, "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 3, p. 975.
21. c) K. Tomooka, T. Igarashi, N. Komine, and T. Nakai, Yuki Gosei Kagaku Kyokaishi, 53, 480 (1995).