Enantioselective [2,3]-wittig rearrangement via a chiral boron ester enolate

Heterocycles

Volumn 42, Issue 1, 1996, Pages 423-435

  Fujimoto, Katsuhiko ^a   Matsuhashi, Chiho ^a   Nakai, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001008691     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s67     Document Type: Article

References (39)

1. A visiting research fellow from Sankyo Co., Tokyo.
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3. Reviews: T. Nakai and K. Mikami, Chem. Rev., 1986, 86, 885; K. Mikami and T. Nakai, Synthesis, 1991, 594; T. Nakai and K. Mikami, Org. React, 1994, 46, 105.
4. Reviews: T. Nakai and K. Mikami, Chem. Rev., 1986, 86, 885; K. Mikami and T. Nakai, Synthesis, 1991, 594; T. Nakai and K. Mikami, Org. React, 1994, 46, 105.
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10. For the enantioselective versions of different [2,3]-Wittig variants (25-70%ee) with chiral lithium amide bases: J. A. Marshall and J. Lebreton, J. Am. Chem. Soc., 1988, 110, 2925; Idem, Tetrahedron Lett., 1987, 28, 3323; Idem, J. Org. Chem., 1988, 53, 4108; J. A. Marshall and X. J. Wang, Ibid., 1990, 55, 2995.
11. For the enantioselective versions of different [2,3]-Wittig variants (25-70%ee) with chiral lithium amide bases: J. A. Marshall and J. Lebreton, J. Am. Chem. Soc., 1988, 110, 2925; Idem, Tetrahedron Lett., 1987, 28, 3323; Idem, J. Org. Chem., 1988, 53, 4108; J. A. Marshall and X. J. Wang, Ibid., 1990, 55, 2995.
12. For the enantioselective versions of different [2,3]-Wittig variants (25-70%ee) with chiral lithium amide bases: J. A. Marshall and J. Lebreton, J. Am. Chem. Soc., 1988, 110, 2925; Idem, Tetrahedron Lett., 1987, 28, 3323; Idem, J. Org. Chem., 1988, 53, 4108; J. A. Marshall and X. J. Wang, Ibid., 1990, 55, 2995.
13. For the enantioselective versions of different [2,3]-Wittig variants (25-70%ee) with chiral lithium amide bases: J. A. Marshall and J. Lebreton, J. Am. Chem. Soc., 1988, 110, 2925; Idem, Tetrahedron Lett., 1987, 28, 3323; Idem, J. Org. Chem., 1988, 53, 4108; J. A. Marshall and X. J. Wang, Ibid., 1990, 55, 2995.
14. A part of this work has appeared as a preliminary form: K. Fujimoto and T. Nakai, Tetrahedron Lett., 1994, 35, 5019.
15. 2BX (X=Cl, Br, I, OTf) failed; no [2,3]-Wittig product was obtained.
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22. 2BOTf].
23. (b) Our unpublished result (ref. 5). The rearrangement with 9-BBNOTf was found to exhibit 95% of erythro selection.
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