Enantioselective [1,2] Wittig rearrangement using an external chiral ligand

Angewandte Chemie - International Edition

Volumn 38, Issue 24, 1999, Pages 3741-3743

  Tomooka, Katsuhiko ^a   Yamamoto, Kyoko ^a   Nakai, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Asymmetric catalysis; Asymmetric synthesis; Rearrangements; Wittig reactions

Indexed keywords

BENZYL ALCOHOL DERIVATIVE; ETHER DERIVATIVE; LIGAND; ORGANOLITHIUM COMPOUND; OXAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033576711     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991216)38:24<3741::AID-ANIE3741>3.0.CO;2-5     Document Type: Article

References (31)

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8. e) K. Tomooka, H. Yamamoto, T. Nakai, Liebigs Ann. Chem. 1997, 1275-1281.
9. 1 is an allylic moiety the rearrangement proceeds overwhelmingly in the symmetry-allowed [2,3]-sigmatropic fashion. Reviews on the [2,3] Wittig rearrangement: ref. [2b, c]; T. Nakai, M. Mikami, Chem. Rev. 1986, 86, 885-902; T. Nakai, M. Mikami, Org. React. 1994, 46, 105-209.
10. 1 is an allylic moiety the rearrangement proceeds overwhelmingly in the symmetry-allowed [2,3]-sigmatropic fashion. Reviews on the [2,3] Wittig rearrangement: ref. [2b, c]; T. Nakai, M. Mikami, Chem. Rev. 1986, 86, 885-902; T. Nakai, M. Mikami, Org. React. 1994, 46, 105-209.
11. Reviews on asymmetric lithiation protocols mostly with (-)-sparteine as the external chiral ligand: a) P. Beak, A. Basu, D. J. Gallagher, Y. S. Park, S. Thayumanavan, Acc. Chem. Res. 1996, 29, 552-560;
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14. Prepared by the reported method: S. E. Denmark, N. Nakajima, O. J.-C. Nicaise, A. M. Faucher, J. P. Edwards, J. Org. Chem. 1995, 60, 4884-4892.
15. Reviews on asymmetric reactions mediated by chiral bis(dihydrooxazol)s; a) C. Bolm, Angew. Chem. 1991, 103, 556-558; Angew. Chem. Int. Ed. Engl. 1991, 30, 542-543;
16. Reviews on asymmetric reactions mediated by chiral bis(dihydrooxazol)s; a) C. Bolm, Angew. Chem. 1991, 103, 556-558; Angew. Chem. Int. Ed. Engl. 1991, 30, 542-543;
17. b) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339-345;
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20. synthetic utilities of chiral bis(dihydrooxazol)/alkyllithium complexes: d) asymmetric addition to imines: S. E. Denmark, N. Nakajima, O. J.-C. Nicaise, J. Am. Chem. Soc. 1994, 116, 8797-8798:
21. e) enantioselective rearrangement of epoxides: D. M. Hodgson, G. P. Lee, Tetrahedron: Asymmetry 1997, 8, 2303-2306;
22. f) enantioselective [2,3] Wittig rearrangement: K. Tomooka, N. Komine, T. Nakai, Tetrahedron Lett. 1998, 38, 5513-5516.
23. D = + 55.9 (c = 1.40 in EtOH) in the literature: G. Berti, F. Bottani, P. L. Ferrarini, B. Macchia, J. Org. Chem. 1965, 30, 4091-4096.
24. When sBuLi/(-)-sparteine was used instead of tBuLi/3, (S)-2 was obtained in 36% yield and with 24% ee, and 1 was recovered in 66% yield.
25. When the reaction temperature was lowered to - 110 C, 71% ee was observed with 37% chemical yield.
26. T. F. Bates, M. T. Clarke, R. D. Thomas, J. Am. Chem. Soc. 1988, 110, 5109-5112.
27. Treatment of 1 with tBuLi alone in diethyl ether under the same conditions did not gave any trace of 2. In sharp contrast, the reaction in THF gave 2 in 70% yield.
28. For the chemistry of RLi/R'OLi complexes, see P. Caubetre, Chem. Rev. 1993, 93, 2317-2334.
29. We found that the separately premixed tBuLi/lithium alkoxide of 2 is not reactive enough to induce the rearrangement.
30. The rearrangement of 4 and 6b with 10 mol% of 3 resulted in 53% ee (56%) and 54% ee (35%), respectively.
31. 3) in the literature: H. R. Sullivan, J. R. Beck, A. Pohland, J. Org. Chem. 1963, 28, 2381-2385.