A New Asymmetric Formylation of Aldehydes

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 3, 1997, Pages 253-255

  Kirschning, Andreas ^a   Dräger, Gerald ^a   Jung, Alexander ^a  

^a CLAUSTHAL UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Asymmetric synthesis; Wittig reactions

Indexed keywords

EID: 0030895728     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199702531     Document Type: Article

References (33)

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8. L. Colombo, M. Di Giacomo, G. Brusotti, E. Milano, Tetrahedron Lett. 1995, 36, 2863-2866; G. Delogu, O. De Lucchi, P. Maglioli, G. Valle, J. Org. Chem. 1991, 56, 4467-4473; H. Mahler, M. Braun, Chem. Ber. 1991, 124, 1379-1395; V. K. Aggarwal, I. W. Davies, J. Maddock, M. F. Mahon, K. C. Molloy, Tetrahedron Lett. 1990, 31, 135-138; V. K. Aggarwal, R. J. Franklin. H. J. Rice, ibid. 1991, 32, 7743-7746; J. E. Lynch, E. L. Eliel, J. Am. Chem. Soc. 1984, 106, 2943-2948; T. S. Abram, R. Baker, C. M. Exon, V. B. Rao, R. W. Turner, J. Chem. Soc. Perkin Trans. 1 1982, 301-306; D. Enders, H. Lotter, Angew. Chem. 1981, 93, 831-832; Angew. Chem. Int. Ed. Engl. 1981, 20, 795-796.
9. L. Colombo, M. Di Giacomo, G. Brusotti, E. Milano, Tetrahedron Lett. 1995, 36, 2863-2866; G. Delogu, O. De Lucchi, P. Maglioli, G. Valle, J. Org. Chem. 1991, 56, 4467-4473; H. Mahler, M. Braun, Chem. Ber. 1991, 124, 1379-1395; V. K. Aggarwal, I. W. Davies, J. Maddock, M. F. Mahon, K. C. Molloy, Tetrahedron Lett. 1990, 31, 135-138; V. K. Aggarwal, R. J. Franklin. H. J. Rice, ibid. 1991, 32, 7743-7746; J. E. Lynch, E. L. Eliel, J. Am. Chem. Soc. 1984, 106, 2943-2948; T. S. Abram, R. Baker, C. M. Exon, V. B. Rao, R. W. Turner, J. Chem. Soc. Perkin Trans. 1 1982, 301-306; D. Enders, H. Lotter, Angew. Chem. 1981, 93, 831-832; Angew. Chem. Int. Ed. Engl. 1981, 20, 795-796.
10. L. Colombo, M. Di Giacomo, G. Brusotti, E. Milano, Tetrahedron Lett. 1995, 36, 2863-2866; G. Delogu, O. De Lucchi, P. Maglioli, G. Valle, J. Org. Chem. 1991, 56, 4467-4473; H. Mahler, M. Braun, Chem. Ber. 1991, 124, 1379-1395; V. K. Aggarwal, I. W. Davies, J. Maddock, M. F. Mahon, K. C. Molloy, Tetrahedron Lett. 1990, 31, 135-138; V. K. Aggarwal, R. J. Franklin. H. J. Rice, ibid. 1991, 32, 7743-7746; J. E. Lynch, E. L. Eliel, J. Am. Chem. Soc. 1984, 106, 2943-2948; T. S. Abram, R. Baker, C. M. Exon, V. B. Rao, R. W. Turner, J. Chem. Soc. Perkin Trans. 1 1982, 301-306; D. Enders, H. Lotter, Angew. Chem. 1981, 93, 831-832; Angew. Chem. Int. Ed. Engl. 1981, 20, 795-796.
11. L. Colombo, M. Di Giacomo, G. Brusotti, E. Milano, Tetrahedron Lett. 1995, 36, 2863-2866; G. Delogu, O. De Lucchi, P. Maglioli, G. Valle, J. Org. Chem. 1991, 56, 4467-4473; H. Mahler, M. Braun, Chem. Ber. 1991, 124, 1379-1395; V. K. Aggarwal, I. W. Davies, J. Maddock, M. F. Mahon, K. C. Molloy, Tetrahedron Lett. 1990, 31, 135-138; V. K. Aggarwal, R. J. Franklin. H. J. Rice, ibid. 1991, 32, 7743-7746; J. E. Lynch, E. L. Eliel, J. Am. Chem. Soc. 1984, 106, 2943-2948; T. S. Abram, R. Baker, C. M. Exon, V. B. Rao, R. W. Turner, J. Chem. Soc. Perkin Trans. 1 1982, 301-306; D. Enders, H. Lotter, Angew. Chem. 1981, 93, 831-832; Angew. Chem. Int. Ed. Engl. 1981, 20, 795-796.
12. L. Colombo, M. Di Giacomo, G. Brusotti, E. Milano, Tetrahedron Lett. 1995, 36, 2863-2866; G. Delogu, O. De Lucchi, P. Maglioli, G. Valle, J. Org. Chem. 1991, 56, 4467-4473; H. Mahler, M. Braun, Chem. Ber. 1991, 124, 1379-1395; V. K. Aggarwal, I. W. Davies, J. Maddock, M. F. Mahon, K. C. Molloy, Tetrahedron Lett. 1990, 31, 135-138; V. K. Aggarwal, R. J. Franklin. H. J. Rice, ibid. 1991, 32, 7743-7746; J. E. Lynch, E. L. Eliel, J. Am. Chem. Soc. 1984, 106, 2943-2948; T. S. Abram, R. Baker, C. M. Exon, V. B. Rao, R. W. Turner, J. Chem. Soc. Perkin Trans. 1 1982, 301-306; D. Enders, H. Lotter, Angew. Chem. 1981, 93, 831-832; Angew. Chem. Int. Ed. Engl. 1981, 20, 795-796.
13. L. Colombo, M. Di Giacomo, G. Brusotti, E. Milano, Tetrahedron Lett. 1995, 36, 2863-2866; G. Delogu, O. De Lucchi, P. Maglioli, G. Valle, J. Org. Chem. 1991, 56, 4467-4473; H. Mahler, M. Braun, Chem. Ber. 1991, 124, 1379-1395; V. K. Aggarwal, I. W. Davies, J. Maddock, M. F. Mahon, K. C. Molloy, Tetrahedron Lett. 1990, 31, 135-138; V. K. Aggarwal, R. J. Franklin. H. J. Rice, ibid. 1991, 32, 7743-7746; J. E. Lynch, E. L. Eliel, J. Am. Chem. Soc. 1984, 106, 2943-2948; T. S. Abram, R. Baker, C. M. Exon, V. B. Rao, R. W. Turner, J. Chem. Soc. Perkin Trans. 1 1982, 301-306; D. Enders, H. Lotter, Angew. Chem. 1981, 93, 831-832; Angew. Chem. Int. Ed. Engl. 1981, 20, 795-796.
14. E. J. Corey, G. B. Jones, Tetrahedron Lett. 1991, 32, 5713-5716.
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16. Reviews on the Horner-Wittig reaction: J. Clayden, S. Warren, Angew. Chem. 1996, 108, 261-291; Angew. Chem. Int. Ed. Engl. 1996, 35, 241-270; B. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989, 89, 863-927.
17. Reviews on the Horner-Wittig reaction: J. Clayden, S. Warren, Angew. Chem. 1996, 108, 261-291; Angew. Chem. Int. Ed. Engl. 1996, 35, 241-270; B. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989, 89, 863-927.
18. Reviews on the asymmetric dihydroxylation: D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1050-1064; H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, pp. 227-272.
19. Reviews on the asymmetric dihydroxylation: D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1050-1064; H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, pp. 227-272.
20. Reviews on the asymmetric dihydroxylation: D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1050-1064; H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, pp. 227-272.
21. Reviews on the asymmetric dihydroxylation: D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1050-1064; H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, pp. 227-272.
22. W. Dietsche, Liebigs Ann. Chem. 1968, 712, 21-27.
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24. Metalation of diethoxymethyl diphenyl phosphine oxide with alternative bases like nBuLi or lithium/potassium hexamethyldisilazide (LHMDA or KHMDA) was incomplete.
25. In accordance with ref. [9], ketene O,O-acetal 1 can also be prepared by direct elimination of the metalated adduct at elevated temperature. However, this procedure gave reduced yields of α-hydroxy carboxylates after AD.
26. For alternative strategies of the asymmetric α-hydroxylation or α-acetoxylation of carboxylates and enolates see Y. Wei, R. Bakthavatchalam, X.-M. Jin, C. K. Murphy, F. A. Davis, Tetrahedron Lett. 1993, 34, 3715-3718; D. Enders, V. Bushan, ibid. 1988, 29, 2437-2440; R. Gamboni, C. Tamm, Helv. Chim. Acta 1986, 69, 615-620; W Oppolzer, P. Dudfield, ibid. 1985, 68, 216-219.
27. For alternative strategies of the asymmetric α-hydroxylation or α-acetoxylation of carboxylates and enolates see Y. Wei, R. Bakthavatchalam, X.-M. Jin, C. K. Murphy, F. A. Davis, Tetrahedron Lett. 1993, 34, 3715-3718; D. Enders, V. Bushan, ibid. 1988, 29, 2437-2440; R. Gamboni, C. Tamm, Helv. Chim. Acta 1986, 69, 615-620; W Oppolzer, P. Dudfield, ibid. 1985, 68, 216-219.
28. For alternative strategies of the asymmetric α-hydroxylation or α-acetoxylation of carboxylates and enolates see Y. Wei, R. Bakthavatchalam, X.-M. Jin, C. K. Murphy, F. A. Davis, Tetrahedron Lett. 1993, 34, 3715-3718; D. Enders, V. Bushan, ibid. 1988, 29, 2437-2440; R. Gamboni, C. Tamm, Helv. Chim. Acta 1986, 69, 615-620; W Oppolzer, P. Dudfield, ibid. 1985, 68, 216-219.
29. For alternative strategies of the asymmetric α-hydroxylation or α-acetoxylation of carboxylates and enolates see Y. Wei, R. Bakthavatchalam, X.-M. Jin, C. K. Murphy, F. A. Davis, Tetrahedron Lett. 1993, 34, 3715-3718; D. Enders, V. Bushan, ibid. 1988, 29, 2437-2440; R. Gamboni, C. Tamm, Helv. Chim. Acta 1986, 69, 615-620; W Oppolzer, P. Dudfield, ibid. 1985, 68, 216-219.
30. H. Becker, K. B. Sharpless, Angew. Chem. 1996, 108, 447-449; Angew. Chem. Int. Ed. Engl. 1996, 35, 448-451.
31. H. Becker, K. B. Sharpless, Angew. Chem. 1996, 108, 447-449; Angew. Chem. Int. Ed. Engl. 1996, 35, 448-451.
32. H. Becker, S. B. King, M. Taniguchi, K. P. M. Vanhessche, K. B. Sharpless, J. Org. Chem. 1995, 60, 3940-3941.
33. KDA was prepared by addition of freshly sublimed KOtBu in THF to an equal amount of LDA at -110 °C.