An asymmetric domino three-component synthesis of β-lactams

European Journal of Organic Chemistry

Volumn , Issue 10, 1998, Pages 2201-2207

  Palomo, Claudio ^a   Aizpurua, Jesús M ^a   Gracenea, José Javier ^a   García Granda, Santiago ^b   Pertierra, Pilar ^b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Antibiotics; Asymmetric synthesis; Michael additions; Multicomponent reactions; Lactams

Indexed keywords

EID: 0002701053     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199810)1998:10<2201::AID-EJOC2201>3.0.CO;2-R     Document Type: Article

References (65)

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2. For reviews on this subject, see: [1a] R. Southgate, S. Elson in Progress in the Chemistry of Organic Natural Products, vol. 47 (Eds.: W. Herz, H. Grisebach, G. W. Kirby, C. Tamm), Springer, Vienna, 1985, p. 1. [1b] R. Southgate, C. Branch, S. Coulton, E. Hunt in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, vol. 2 (Ed.: G. Lukacs), Springer, Berlin, 1993, p. 621. [1c] R. Southgate, Contemp. Org. Synth 1994, 1, 417-432. [1d] The Chemistry of β-Lactams (Ed.: M. I. Page), Chapman and Hall, London, 1992.
3. For reviews on this subject, see: [1a] R. Southgate, S. Elson in Progress in the Chemistry of Organic Natural Products, vol. 47 (Eds.: W. Herz, H. Grisebach, G. W. Kirby, C. Tamm), Springer, Vienna, 1985, p. 1. [1b] R. Southgate, C. Branch, S. Coulton, E. Hunt in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, vol. 2 (Ed.: G. Lukacs), Springer, Berlin, 1993, p. 621. [1c] R. Southgate, Contemp. Org. Synth 1994, 1, 417-432. [1d] The Chemistry of β-Lactams (Ed.: M. I. Page), Chapman and Hall, London, 1992.
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17. For recent general reviews on β-lactam synthesis, see: [6a] J. Backes, in Houben-Weyl. Methoden Org. Chem. 1991, vol E 16B, p. 31. [6b] N. Dekimpe, in Comprehensive Heterocyclic Chemistry II, vol. 1B (Ed.: A. Padwa), 1996, p. 507. -For recent reviews on asymmetric synthesis of β-lactams, see: [6c] R. C. Thomas, in Recent Progress in the Chemical Synthesis of Antibiotics, vol. 1 (Eds.: G. Lukacs, M. Ohno), Springer, Berlin, 1990, p. 533. [6d] R. J. Ternansky, J. M. Morin, Jr., in The Organic Chemistry of β-Lactams (Ed.: G. I. Georg), VCH, New York, 1993, p. 257. [6e] L. Ghosez, J. Marchand-Brynaert, in Comprehensive Organic Synthesis, vol. 5 (Eds.: B. Trost, I. Fleming), Pergamon, Oxford. 1991, p. 85.
18. For reviews, see: [7a] D. J. Hart, D. C. Ha, Chem. Rev. 1989, 89, 1447-1465. [7b] M. J. Brown, Heterocycles 1989, 29, 2225-2244. [7c] G. I. Georg, in Studies in Natural Product Chemistry, vol. 4 (Ed.: A.-ur Rahman), Elsevier, Amsterdam, 1989, p. 431. [7d] T. Fujisawa, M Shimizu, Rev. Heteroatom Chem. 1996, 15, 203-225. [7e] G. Cainelli, M. Panunzio, D. Giacomini, G. Martelli, G. Spunta, E. Bandini, in Chemical Synthesis, Gnosis to Prognosis (Eds.: C. Chatgilialoglu, V. Snieckus), Kluwer Academic, Amsterdam, 1996, p. 25.
19. For reviews, see: [7a] D. J. Hart, D. C. Ha, Chem. Rev. 1989, 89, 1447-1465. [7b] M. J. Brown, Heterocycles 1989, 29, 2225-2244. [7c] G. I. Georg, in Studies in Natural Product Chemistry, vol. 4 (Ed.: A.-ur Rahman), Elsevier, Amsterdam, 1989, p. 431. [7d] T. Fujisawa, M Shimizu, Rev. Heteroatom Chem. 1996, 15, 203-225. [7e] G. Cainelli, M. Panunzio, D. Giacomini, G. Martelli, G. Spunta, E. Bandini, in Chemical Synthesis, Gnosis to Prognosis (Eds.: C. Chatgilialoglu, V. Snieckus), Kluwer Academic, Amsterdam, 1996, p. 25.
20. For reviews, see: [7a] D. J. Hart, D. C. Ha, Chem. Rev. 1989, 89, 1447-1465. [7b] M. J. Brown, Heterocycles 1989, 29, 2225-2244. [7c] G. I. Georg, in Studies in Natural Product Chemistry, vol. 4 (Ed.: A.-ur Rahman), Elsevier, Amsterdam, 1989, p. 431. [7d] T. Fujisawa, M Shimizu, Rev. Heteroatom Chem. 1996, 15, 203-225. [7e] G. Cainelli, M. Panunzio, D. Giacomini, G. Martelli, G. Spunta, E. Bandini, in Chemical Synthesis, Gnosis to Prognosis (Eds.: C. Chatgilialoglu, V. Snieckus), Kluwer Academic, Amsterdam, 1996, p. 25.
21. For reviews, see: [7a] D. J. Hart, D. C. Ha, Chem. Rev. 1989, 89, 1447-1465. [7b] M. J. Brown, Heterocycles 1989, 29, 2225-2244. [7c] G. I. Georg, in Studies in Natural Product Chemistry, vol. 4 (Ed.: A.-ur Rahman), Elsevier, Amsterdam, 1989, p. 431. [7d] T. Fujisawa, M Shimizu, Rev. Heteroatom Chem. 1996, 15, 203-225. [7e] G. Cainelli, M. Panunzio, D. Giacomini, G. Martelli, G. Spunta, E. Bandini, in Chemical Synthesis, Gnosis to Prognosis (Eds.: C. Chatgilialoglu, V. Snieckus), Kluwer Academic, Amsterdam, 1996, p. 25.
22. For reviews, see: [7a] D. J. Hart, D. C. Ha, Chem. Rev. 1989, 89, 1447-1465. [7b] M. J. Brown, Heterocycles 1989, 29, 2225-2244. [7c] G. I. Georg, in Studies in Natural Product Chemistry, vol. 4 (Ed.: A.-ur Rahman), Elsevier, Amsterdam, 1989, p. 431. [7d] T. Fujisawa, M Shimizu, Rev. Heteroatom Chem. 1996, 15, 203-225. [7e] G. Cainelli, M. Panunzio, D. Giacomini, G. Martelli, G. Spunta, E. Bandini, in Chemical Synthesis, Gnosis to Prognosis (Eds.: C. Chatgilialoglu, V. Snieckus), Kluwer Academic, Amsterdam, 1996, p. 25.
23. For an extensive list of metal enolates used for β-lactam synthesis, see: H. L. van Maanen, H. Kleijn, J. T. B. H. Jastrzebski, J. Verweij, A. P. G. Kieboom, G. van Koten, J. Org. Chem. 1995, 60, 4331-4338.
24. For related approaches to β-lactams involving conjugate addition of amidocuprates to enoates followed by enolate trapping with an aldehyde and subsequent cyclization of the resulting isolated intermediates to the corresponding β-lactam, see: [9a] Y. Yamamoto, N. Asao, T. Uyehara, J. Am. Chem. Soc. 1992, 114, 5427-5429. [9b] N. Asao, T. Uyehara, N. Tsukada, Y. Yamamoto, Bull. Chem. Soc. Jpn. 1995, 68, 2103-2111. [9c] S. G. Davies, D. R. Fenwick, Chem. Commun. 1997, 565-566. [9d] N. Asao, T. Shimada, T. Sudo, N. Tsukada, K. Yazawa, Y. S. Gyoung, T. Uyhehara, Y. Yamamoto, J. Org. Chem. 1997, 62, 6274-6282. - For a comprehensive review on conjugate addition-enolate trapping, see: [9e] M. Hulce, M. J. Chapdelaine, in Comprehensive Organic Synthesis, vol. 4 (Ed.: M. F. Semmelhack), Pergamon, Oxford, 1991, p. 237. - For another approach to β-lactams involving a one-pot reaction of an amine. an aldehyde and silyl ketene thioacetals, see: [9f] R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, O. Schupp, J. Org. Chem. 1996, 61, 8293-8296.
25. For related approaches to β-lactams involving conjugate addition of amidocuprates to enoates followed by enolate trapping with an aldehyde and subsequent cyclization of the resulting isolated intermediates to the corresponding β-lactam, see: [9a] Y. Yamamoto, N. Asao, T. Uyehara, J. Am. Chem. Soc. 1992, 114, 5427-5429. [9b] N. Asao, T. Uyehara, N. Tsukada, Y. Yamamoto, Bull. Chem. Soc. Jpn. 1995, 68, 2103-2111. [9c] S. G. Davies, D. R. Fenwick, Chem. Commun. 1997, 565-566. [9d] N. Asao, T. Shimada, T. Sudo, N. Tsukada, K. Yazawa, Y. S. Gyoung, T. Uyhehara, Y. Yamamoto, J. Org. Chem. 1997, 62, 6274-6282. - For a comprehensive review on conjugate addition-enolate trapping, see: [9e] M. Hulce, M. J. Chapdelaine, in Comprehensive Organic Synthesis, vol. 4 (Ed.: M. F. Semmelhack), Pergamon, Oxford, 1991, p. 237. - For another approach to β-lactams involving a one-pot reaction of an amine. an aldehyde and silyl ketene thioacetals, see: [9f] R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, O. Schupp, J. Org. Chem. 1996, 61, 8293-8296.
26. For related approaches to β-lactams involving conjugate addition of amidocuprates to enoates followed by enolate trapping with an aldehyde and subsequent cyclization of the resulting isolated intermediates to the corresponding β-lactam, see: [9a] Y. Yamamoto, N. Asao, T. Uyehara, J. Am. Chem. Soc. 1992, 114, 5427-5429. [9b] N. Asao, T. Uyehara, N. Tsukada, Y. Yamamoto, Bull. Chem. Soc. Jpn. 1995, 68, 2103-2111. [9c] S. G. Davies, D. R. Fenwick, Chem. Commun. 1997, 565-566. [9d] N. Asao, T. Shimada, T. Sudo, N. Tsukada, K. Yazawa, Y. S. Gyoung, T. Uyhehara, Y. Yamamoto, J. Org. Chem. 1997, 62, 6274-6282. - For a comprehensive review on conjugate addition-enolate trapping, see: [9e] M. Hulce, M. J. Chapdelaine, in Comprehensive Organic Synthesis, vol. 4 (Ed.: M. F. Semmelhack), Pergamon, Oxford, 1991, p. 237. - For another approach to β-lactams involving a one-pot reaction of an amine. an aldehyde and silyl ketene thioacetals, see: [9f] R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, O. Schupp, J. Org. Chem. 1996, 61, 8293-8296.
27. For related approaches to β-lactams involving conjugate addition of amidocuprates to enoates followed by enolate trapping with an aldehyde and subsequent cyclization of the resulting isolated intermediates to the corresponding β-lactam, see: [9a] Y. Yamamoto, N. Asao, T. Uyehara, J. Am. Chem. Soc. 1992, 114, 5427-5429. [9b] N. Asao, T. Uyehara, N. Tsukada, Y. Yamamoto, Bull. Chem. Soc. Jpn. 1995, 68, 2103-2111. [9c] S. G. Davies, D. R. Fenwick, Chem. Commun. 1997, 565-566. [9d] N. Asao, T. Shimada, T. Sudo, N. Tsukada, K. Yazawa, Y. S. Gyoung, T. Uyhehara, Y. Yamamoto, J. Org. Chem. 1997, 62, 6274-6282. - For a comprehensive review on conjugate addition-enolate trapping, see: [9e] M. Hulce, M. J. Chapdelaine, in Comprehensive Organic Synthesis, vol. 4 (Ed.: M. F. Semmelhack), Pergamon, Oxford, 1991, p. 237. - For another approach to β-lactams involving a one-pot reaction of an amine. an aldehyde and silyl ketene thioacetals, see: [9f] R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, O. Schupp, J. Org. Chem. 1996, 61, 8293-8296.
28. For related approaches to β-lactams involving conjugate addition of amidocuprates to enoates followed by enolate trapping with an aldehyde and subsequent cyclization of the resulting isolated intermediates to the corresponding β-lactam, see: [9a] Y. Yamamoto, N. Asao, T. Uyehara, J. Am. Chem. Soc. 1992, 114, 5427-5429. [9b] N. Asao, T. Uyehara, N. Tsukada, Y. Yamamoto, Bull. Chem. Soc. Jpn. 1995, 68, 2103-2111. [9c] S. G. Davies, D. R. Fenwick, Chem. Commun. 1997, 565-566. [9d] N. Asao, T. Shimada, T. Sudo, N. Tsukada, K. Yazawa, Y. S. Gyoung, T. Uyhehara, Y. Yamamoto, J. Org. Chem. 1997, 62, 6274-6282. - For a comprehensive review on conjugate addition-enolate trapping, see: [9e] M. Hulce, M. J. Chapdelaine, in Comprehensive Organic Synthesis, vol. 4 (Ed.: M. F. Semmelhack), Pergamon, Oxford, 1991, p. 237. - For another approach to β-lactams involving a one-pot reaction of an amine. an aldehyde and silyl ketene thioacetals, see: [9f] R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, O. Schupp, J. Org. Chem. 1996, 61, 8293-8296.
29. For related approaches to β-lactams involving conjugate addition of amidocuprates to enoates followed by enolate trapping with an aldehyde and subsequent cyclization of the resulting isolated intermediates to the corresponding β-lactam, see: [9a] Y. Yamamoto, N. Asao, T. Uyehara, J. Am. Chem. Soc. 1992, 114, 5427-5429. [9b] N. Asao, T. Uyehara, N. Tsukada, Y. Yamamoto, Bull. Chem. Soc. Jpn. 1995, 68, 2103-2111. [9c] S. G. Davies, D. R. Fenwick, Chem. Commun. 1997, 565-566. [9d] N. Asao, T. Shimada, T. Sudo, N. Tsukada, K. Yazawa, Y. S. Gyoung, T. Uyhehara, Y. Yamamoto, J. Org. Chem. 1997, 62, 6274-6282. - For a comprehensive review on conjugate addition-enolate trapping, see: [9e] M. Hulce, M. J. Chapdelaine, in Comprehensive Organic Synthesis, vol. 4 (Ed.: M. F. Semmelhack), Pergamon, Oxford, 1991, p. 237. - For another approach to β-lactams involving a one-pot reaction of an amine. an aldehyde and silyl ketene thioacetals, see: [9f] R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, O. Schupp, J. Org. Chem. 1996, 61, 8293-8296.
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33. For reviews on asymmetric conjugate additions, see: [11a] B. E. Rossiter, N. M. Swingle, Chem. Rev. 1992, 92, 771-806. [11b] H.-G. Schmalz, in Comprehensive Organic Synthesis, vol. 4 (Ed.: M. F. Semmelhack), Pergamon, Oxford, 1991, p. 199-236. [11c] J. Leonard, Contemp. Org. Synth. 1994, 1, 387-414. [11d] P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992.
34. For reviews on asymmetric conjugate additions, see: [11a] B. E. Rossiter, N. M. Swingle, Chem. Rev. 1992, 92, 771-806. [11b] H.-G. Schmalz, in Comprehensive Organic Synthesis, vol. 4 (Ed.: M. F. Semmelhack), Pergamon, Oxford, 1991, p. 199-236. [11c] J. Leonard, Contemp. Org. Synth. 1994, 1, 387-414. [11d] P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992.
35. For reviews on asymmetric conjugate additions, see: [11a] B. E. Rossiter, N. M. Swingle, Chem. Rev. 1992, 92, 771-806. [11b] H.-G. Schmalz, in Comprehensive Organic Synthesis, vol. 4 (Ed.: M. F. Semmelhack), Pergamon, Oxford, 1991, p. 199-236. [11c] J. Leonard, Contemp. Org. Synth. 1994, 1, 387-414. [11d] P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992.
36. For the addition of organocuprate reagents to azomethine functions, see: [12a] G. Alvaro, D. Savoia, M. R. Valentinetti, Tetrahedron 1996, 52, 12571-12586. [12b] K. Ishimaru, K. Tsuru, K. Yabuta, M. Wada, Y. Yamamoto, K.-Y. Akiba, Tetrahedron 1996, 52, 13137-13144.
37. For the addition of organocuprate reagents to azomethine functions, see: [12a] G. Alvaro, D. Savoia, M. R. Valentinetti, Tetrahedron 1996, 52, 12571-12586. [12b] K. Ishimaru, K. Tsuru, K. Yabuta, M. Wada, Y. Yamamoto, K.-Y. Akiba, Tetrahedron 1996, 52, 13137-13144.
38. 13C-NMR spectra were obtained after preparative HPLC separation.
39. For leading references on conjugate additions by using both 8 and 9, see: [14a] W. Oppolzer, Tetrahedron 1987, 43, 1969-2004. [14b] C. Palomo, J. M. Aizpurua, M. Iturburu, R. Urchegui, J. Org. Chem 1994, 59, 240-244. [14c] X. Qian, K. C. Russell, L. U. Botegu, V. J. Hruby, Tetrahedron 1995, 51, 1033-1054. [14d] E. Nicolas, K. C. Russell, J. Knollenberg, V. J. Hruby, J Org. Chem. 1993, 58, 766-770.
40. For leading references on conjugate additions by using both 8 and 9, see: [14a] W. Oppolzer, Tetrahedron 1987, 43, 1969-2004. [14b] C. Palomo, J. M. Aizpurua, M. Iturburu, R. Urchegui, J. Org. Chem 1994, 59, 240-244. [14c] X. Qian, K. C. Russell, L. U. Botegu, V. J. Hruby, Tetrahedron 1995, 51, 1033-1054. [14d] E. Nicolas, K. C. Russell, J. Knollenberg, V. J. Hruby, J Org. Chem. 1993, 58, 766-770.
41. For leading references on conjugate additions by using both 8 and 9, see: [14a] W. Oppolzer, Tetrahedron 1987, 43, 1969-2004. [14b] C. Palomo, J. M. Aizpurua, M. Iturburu, R. Urchegui, J. Org. Chem 1994, 59, 240-244. [14c] X. Qian, K. C. Russell, L. U. Botegu, V. J. Hruby, Tetrahedron 1995, 51, 1033-1054. [14d] E. Nicolas, K. C. Russell, J. Knollenberg, V. J. Hruby, J Org. Chem. 1993, 58, 766-770.
42. For leading references on conjugate additions by using both 8 and 9, see: [14a] W. Oppolzer, Tetrahedron 1987, 43, 1969-2004. [14b] C. Palomo, J. M. Aizpurua, M. Iturburu, R. Urchegui, J. Org. Chem 1994, 59, 240-244. [14c] X. Qian, K. C. Russell, L. U. Botegu, V. J. Hruby, Tetrahedron 1995, 51, 1033-1054. [14d] E. Nicolas, K. C. Russell, J. Knollenberg, V. J. Hruby, J Org. Chem. 1993, 58, 766-770.
43. In general, glyoxylate imines do not react well with enolates, particularly with lithium enolates, to give β-lactams, see: G. I. Georg, J. Kant, H. S. Gill, J. Am. Chem. Soc. 1987, 109, 1129.
44. D. J. Hart, C-S. Lee, J Am. Chem. Soc. 1986, 108, 6054-6056. In our hands, 17 upon treatment with LDA and the imine 18 gave a 70% yield of 19 as a 87:13 mixture of cisltrans diastereomers [e.e: 46% for the (3R,4R)-cis enantiomer].
45. C. Palomo, F. P. Cossio, J. M. Ontoria, J. M. Odriozola, J. Org. Chem. 1991, 56, 5948-5951.
46. 2]/3. Total number of parameters 451. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crytallographic Data Centre as supplementary publication no. CCDC-101498. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: int, code + 44(1223)336-033; E-mail: deposit@ccdc.cam.ac.uk].
47. 2CuLi with imine 10 in THF at 0°C for 3 h did not afford any imine addition compound and the polymerization of the imine was observed instead. For recent reviews on domino reactions, see: [19a] L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170; Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163. [19b] L. F. Tietze, Chem. Rev. 1996, 96, 115-136.
48. 2CuLi with imine 10 in THF at 0°C for 3 h did not afford any imine addition compound and the polymerization of the imine was observed instead. For recent reviews on domino reactions, see: [19a] L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170; Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163. [19b] L. F. Tietze, Chem. Rev. 1996, 96, 115-136.
49. 2CuLi with imine 10 in THF at 0°C for 3 h did not afford any imine addition compound and the polymerization of the imine was observed instead. For recent reviews on domino reactions, see: [19a] L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170; Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163. [19b] L. F. Tietze, Chem. Rev. 1996, 96, 115-136.
50. 2CuLi and Michael acceptor 11 at 0°C was also examined. equation presented While 24 gave the expected mixture of cis- and trans-β-lactams (57:43) in very poor yield (< 10%), 25 gave a 50:50 mixture of the corresponding β-N-Boc-aminoamides, which did not cyclize to the corresponding β-lactams. For a related two-component reaction of activated imines with enolates from chiral N-acyloxazolidinones and Oppolzer's camphorsultam derivatives, see: [20a] I. Abrahams, M. Motevalli, A. J. Robinson, P. B. Wyatt, Tetrahedron 1994, 50, 12755-12772. [20b] A. M. Kanazawa, J.-N. Denis, A. E. Greene, J. Org. Chem. 1994, 59, 1238-1240.
51. 2CuLi and Michael acceptor 11 at 0°C was also examined. equation presented While 24 gave the expected mixture of cis- and trans-β-lactams (57:43) in very poor yield (< 10%), 25 gave a 50:50 mixture of the corresponding β-N-Boc-aminoamides, which did not cyclize to the corresponding β-lactams. For a related two-component reaction of activated imines with enolates from chiral N-acyloxazolidinones and Oppolzer's camphorsultam derivatives, see: [20a] I. Abrahams, M. Motevalli, A. J. Robinson, P. B. Wyatt, Tetrahedron 1994, 50, 12755-12772. [20b] A. M. Kanazawa, J.-N. Denis, A. E. Greene, J. Org. Chem. 1994, 59, 1238-1240.
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