Enantioselective diels - Alder cycloaddition by preorganization on a chiral lewis acid template

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 23, 1997, Pages 2670-2673

  Bienaymé, Hugues ^a  

^a SANOFI   (France)

Author keywords

Asymmetric synthesis; Cycloadditions; TADDOL

Indexed keywords

EID: 0031573948     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199726701     Document Type: Article

References (26)

1. For recent reviews, see: a) T. Oh, M. Reilly, Org. Prep. Proced. Int. 1994, 26, 129-158; b) L. Deloux, M. Srebnik, Chem. Rev. 1993, 93, 763-784; c) H. B. Kagan, O. Riant, ibid. 1992, 92, 1007-1019; d) K. Narasaka, Synthesis 1991, 1-11.
2. For recent reviews, see: a) T. Oh, M. Reilly, Org. Prep. Proced. Int. 1994, 26, 129-158; b) L. Deloux, M. Srebnik, Chem. Rev. 1993, 93, 763-784; c) H. B. Kagan, O. Riant, ibid. 1992, 92, 1007-1019; d) K. Narasaka, Synthesis 1991, 1-11.
3. For recent reviews, see: a) T. Oh, M. Reilly, Org. Prep. Proced. Int. 1994, 26, 129-158; b) L. Deloux, M. Srebnik, Chem. Rev. 1993, 93, 763-784; c) H. B. Kagan, O. Riant, ibid. 1992, 92, 1007-1019; d) K. Narasaka, Synthesis 1991, 1-11.
4. For recent reviews, see: a) T. Oh, M. Reilly, Org. Prep. Proced. Int. 1994, 26, 129-158; b) L. Deloux, M. Srebnik, Chem. Rev. 1993, 93, 763-784; c) H. B. Kagan, O. Riant, ibid. 1992, 92, 1007-1019; d) K. Narasaka, Synthesis 1991, 1-11.
5. On the bonding nature of Lewis acid/carbonyl complexes : a) S. E. Denmark, N. G. Almstead, J. Am. Chem. Soc. 1993, 115, 3133-3139; b) S. Shambayati, W. E. Crowe, S. L. Schreiber, Angew. Chem. 1990, 102, 273; Angew. Chem. Int. Ed. Engl. 1990, 29, 256-272; c) D. M. Birney, K. N. Houk, J. Am. Chem. Soc. 1990, 112, 4127-4133.
6. On the bonding nature of Lewis acid/carbonyl complexes : a) S. E. Denmark, N. G. Almstead, J. Am. Chem. Soc. 1993, 115, 3133-3139; b) S. Shambayati, W. E. Crowe, S. L. Schreiber, Angew. Chem. 1990, 102, 273; Angew. Chem. Int. Ed. Engl. 1990, 29, 256-272; c) D. M. Birney, K. N. Houk, J. Am. Chem. Soc. 1990, 112, 4127-4133.
7. On the bonding nature of Lewis acid/carbonyl complexes : a) S. E. Denmark, N. G. Almstead, J. Am. Chem. Soc. 1993, 115, 3133-3139; b) S. Shambayati, W. E. Crowe, S. L. Schreiber, Angew. Chem. 1990, 102, 273; Angew. Chem. Int. Ed. Engl. 1990, 29, 256-272; c) D. M. Birney, K. N. Houk, J. Am. Chem. Soc. 1990, 112, 4127-4133.
8. On the bonding nature of Lewis acid/carbonyl complexes : a) S. E. Denmark, N. G. Almstead, J. Am. Chem. Soc. 1993, 115, 3133-3139; b) S. Shambayati, W. E. Crowe, S. L. Schreiber, Angew. Chem. 1990, 102, 273; Angew. Chem. Int. Ed. Engl. 1990, 29, 256-272; c) D. M. Birney, K. N. Houk, J. Am. Chem. Soc. 1990, 112, 4127-4133.
9. S. Mutti, C. Daubié, F. Decalorgne, R. Fournier, P. Rossi, Tetrahedron Lett. 1996, 37, 3125-3128; see also: S. Mutti, C. Daubié, J. Malpart, X. Radisson, ibid. 1996, 37, 8743-8746; M. Tabart, J. F. Peyronel, Bioorg. Med. Chem. Lett. 1994, 4, 673-676.
10. S. Mutti, C. Daubié, F. Decalorgne, R. Fournier, P. Rossi, Tetrahedron Lett. 1996, 37, 3125-3128; see also: S. Mutti, C. Daubié, J. Malpart, X. Radisson, ibid. 1996, 37, 8743-8746; M. Tabart, J. F. Peyronel, Bioorg. Med. Chem. Lett. 1994, 4, 673-676.
11. S. Mutti, C. Daubié, F. Decalorgne, R. Fournier, P. Rossi, Tetrahedron Lett. 1996, 37, 3125-3128; see also: S. Mutti, C. Daubié, J. Malpart, X. Radisson, ibid. 1996, 37, 8743-8746; M. Tabart, J. F. Peyronel, Bioorg. Med. Chem. Lett. 1994, 4, 673-676.
12. H. Bienaymé, A. Longeau, Tetrahedron 1997, 53, 9637-9646.
13. This unusual dienolate preparation is likely favored by the relatively high reactivity of enol acetates in Ti-promoted transesterification reactions.
14. J. A. Ibers, Nature 1963, 197, 686-687.
15. A. K. Beck, B. Bastani, D. A. Plattner, W. Petter, D. Seebach, H. Braunschweiger, P. Gysi, L. La Vecchia, Chimia 1991, 45, 238-244.
16. Np-TADDOL is a highly efficient ligand for the asymmetric addition of organozinc reagents to aldehydes: a) D. Seebach, D. A. Plattner, A. K. Beck, Y. M. Wang,D. Hunziker, W. Petter, Helv. Chim. Acta 1992, 75, 2171-2209; b) Y. N. Ito, X. Ariza, A. K. Beck, A. Bohac, C Ganter, R. E. Gaw, Y. N. Ito, X. Ariza, A. K. Beck, A. Bohac, C Ganter, R. E. Gawler, F. N. M. Kühnle, J. Tuleja, Y. M. Wang, D. Seebach, Helv. Chim. Acta 1994, 77, 2071 -2110.
17. Np-TADDOL is a highly efficient ligand for the asymmetric addition of organozinc reagents to aldehydes: a) D. Seebach, D. A. Plattner, A. K. Beck, Y. M. Wang,D. Hunziker, W. Petter, Helv. Chim. Acta 1992, 75, 2171-2209; b) Y. N. Ito, X. Ariza, A. K. Beck, A. Bohac, C Ganter, R. E. Gaw, Y. N. Ito, X. Ariza, A. K. Beck, A. Bohac, C Ganter, R. E. Gawler, F. N. M. Kühnle, J. Tuleja, Y. M. Wang, D. Seebach, Helv. Chim. Acta 1994, 77, 2071 -2110.
18. The scope of the first efficient asymmetric cycloadditions involving N-substituted maleimides was narrow, and the maleimide N-substituents are not easily removed: E. J. Corey, S. Sarshar, D. H. Lee, J. Am. Chem. Soc. 1994, 116, 12089-12090.
19. 4/racTADDOL). None of these controls exhibited a diastereomer ratio exceeding 60:40, a result indicating that (R)-α-methylbenzylmaleimide is not responsible for the enantiocontrol in cycloaddition leading to 4. Furthermore, (R)-α-methylbenzylmaleimide is known to be a weakly diastereoselective dienophile in substrate-controlled Diels-Alder cycloadditions: S. W. Baldwin, P. Greenspan, C. Alaimo, A. T. McPhail, Tetrahedron Lett. 1991, 32, 5877-5880.
20. The absolute stereochemistry shown in Scheme 2 is opposite to that required for the construction of the RPR 107880 core. However, this is of little concern, since both antipodal forms of TADDOL ligands are equally available from tartrate esters.
21. For recent reviews on TADDOL-mediated reactions, see: a) M.Braun, Angew: Chem. 1996, 108, 565-568; Angew. Chem. Int. Ed. Engl. 1996, 35, 519-522; b) R. Dahinden, A. K. Beck. D. Seebach in Encyclopedia of Reagents for Organic Synthesis, Vol. 3 (Ed.: L. Paquette), Wiley, Chichester, 1995, pp. 2167-2170; c) R. O. Duthaler, A. Hafner, P. A. Alsters, P. Rothe-Streit, G. Rihs, Pure Appl. Client. 1992,64,1897-1910; d) K. Narasaka, ibid. 1992, 64, 1889-1896.
22. For recent reviews on TADDOL-mediated reactions, see: a) M.Braun, Angew: Chem. 1996, 108, 565-568; Angew. Chem. Int. Ed. Engl. 1996, 35, 519-522; b) R. Dahinden, A. K. Beck. D. Seebach in Encyclopedia of Reagents for Organic Synthesis, Vol. 3 (Ed.: L. Paquette), Wiley, Chichester, 1995, pp. 2167-2170; c) R. O. Duthaler, A. Hafner, P. A. Alsters, P. Rothe-Streit, G. Rihs, Pure Appl. Client. 1992,64,1897-1910; d) K. Narasaka, ibid. 1992, 64, 1889-1896.
23. For recent reviews on TADDOL-mediated reactions, see: a) M.Braun, Angew: Chem. 1996, 108, 565-568; Angew. Chem. Int. Ed. Engl. 1996, 35, 519-522; b) R. Dahinden, A. K. Beck. D. Seebach in Encyclopedia of Reagents for Organic Synthesis, Vol. 3 (Ed.: L. Paquette), Wiley, Chichester, 1995, pp. 2167-2170; c) R. O. Duthaler, A. Hafner, P. A. Alsters, P. Rothe-Streit, G. Rihs, Pure Appl. Client. 1992,64,1897-1910; d) K. Narasaka, ibid. 1992, 64, 1889-1896.
24. For recent reviews on TADDOL-mediated reactions, see: a) M.Braun, Angew: Chem. 1996, 108, 565-568; Angew. Chem. Int. Ed. Engl. 1996, 35, 519-522; b) R. Dahinden, A. K. Beck. D. Seebach in Encyclopedia of Reagents for Organic Synthesis, Vol. 3 (Ed.: L. Paquette), Wiley, Chichester, 1995, pp. 2167-2170; c) R. O. Duthaler, A. Hafner, P. A. Alsters, P. Rothe-Streit, G. Rihs, Pure Appl. Client. 1992,64,1897-1910; d) K. Narasaka, ibid. 1992, 64, 1889-1896.
25. For recent reviews on TADDOL-mediated reactions, see: a) M.Braun, Angew: Chem. 1996, 108, 565-568; Angew. Chem. Int. Ed. Engl. 1996, 35, 519-522; b) R. Dahinden, A. K. Beck. D. Seebach in Encyclopedia of Reagents for Organic Synthesis, Vol. 3 (Ed.: L. Paquette), Wiley, Chichester, 1995, pp. 2167-2170; c) R. O. Duthaler, A. Hafner, P. A. Alsters, P. Rothe-Streit, G. Rihs, Pure Appl. Client. 1992,64,1897-1910; d) K. Narasaka, ibid. 1992, 64, 1889-1896.
26. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallogrphic Data Centre as supplementary publication no. CCDC-100453. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ, UK deposit@chemcrys.cam.ac.uk