Three-component sequential Aza[4+2] cycloaddition/allylboration/retro- sulfinyl-ene reaction: A new stereocontrolled entry to palustrine alkaloids and other 2,6-disubstituted piperidines

Angewandte Chemie - International Edition

Volumn 43, Issue 15, 2004, Pages 2001-2004

  Touré, Barry B ^a   Hall, Dennis G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Allylation; Asymmetric synthesis; Cycloaddition; Multicomponent reactions; Nitrogen heterocycles; Piperidines

Indexed keywords

ALDEHYDES; ALKYLATION; DERIVATIVES;

CHIRAL SULFINIMIDE DIENOPHILES; DIASTEREOSELECTIVITY;

ADDITION REACTIONS;

1,3 BUTADIENE; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; ALLYL COMPOUND; BORONIC ACID DERIVATIVE; HYDRAZONE DERIVATIVE; IMIDE; METHYL GROUP; PIPERIDINE DERIVATIVE; PROTEIN DERIVATIVE; SULFUR DERIVATIVE;

ACCURACY; ALLYLATION; ARTICLE; CHIRALITY; CYCLOADDITION; DERIVATIZATION; MOLECULAR INTERACTION; MOLECULAR MECHANICS; REACTION ANALYSIS; SEQUENTIAL ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; TECHNIQUE;

EID: 4544313802     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200353152     Document Type: Article

References (52)

1. For recent reviews on multicomponent reactions, see: a) L. Weber, K. Illgen, M. Almstetter, Synlett 1999, 366-374;
2. b) A. Dömling, Comb. Chem. High Throughput Screening 1999, 2, 1;
3. c) A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300-3344; Angew. Chem. Int. Ed. 2000, 39, 3169-3210;
4. c) A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300-3344; Angew. Chem. Int. Ed. 2000, 39, 3169-3210;
5. d) H. Bienaymé, C. Hulme, G. Oddon, P. Schmitt, Chem. Eur. J. 2000, 6, 3321-3329;
6. e) J. P. Zhu, Eur. J. Org. Chem. 2003, 1133-1144.
7. For recent examples of applications of multicomponent reactions in target-oriented synthesis, see: a) B. M. Trost, R.I. Higuchi, J. Am. Chem. Soc. 1996, 118, 10 094-10 105;
8. b) L. F. Tietze, Y. F. Zhou, Angew. Chem. 1999,111, 2076-2078; Angew. Chem. Int. Ed. 1999, 38, 2045-2047;
9. b) L. F. Tietze, Y. F. Zhou, Angew. Chem. 1999,111, 2076-2078; Angew. Chem. Int. Ed. 1999, 38, 2045-2047;
10. c) T. Dierkes, A. Fürstner, Org. Lett. 2000, 2, 2463-2466;
11. d) R. Stragies, S. Blechert, J. Am. Chem. Soc. 2000, 122, 9584-9591;
12. e) S. Saito, S. Yamazaki, H. Yamamoto, Angew. Chem. 2001, 113, 3725-3729; Angew. Chem. Int. Ed. 2001, 40, 3613-3617;
13. e) S. Saito, S. Yamazaki, H. Yamamoto, Angew. Chem. 2001, 113, 3725-3729; Angew. Chem. Int. Ed. 2001, 40, 3613-3617;
14. f) L. A. Arnold, R. Naasz, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2001, 123, 5841-5842;
15. g) A. B. Smith III, V. A. Doughty, C. Sfouggatakis, C. S. Bennett, J. Koyanagi, M. Takeuchi, Org. Lett. 2002, 4, 783-786;
16. h) D. A. Powel, R. A. Batey, Org. Lett. 2002, 4, 2913-2916;
17. i) Y. Mi, J. V. Schreiber, E. J. Corey, J. Am. Chem. Soc. 2002, 124, 11290-11291.
18. For the original carbocyclic [4+2] cycloaddition/allylboration tandem reaction, see: a) M. Vaultier, F. Truchet, B. Carboni, R. W. Hoffmann, I. Denne, Tetrahedron Lett. 1987, 28, 4169;
19. b) Y. Six, J.-Y. Lallemand, Tetrahedron Lett. 1999, 40, 1295.
20. a) J. Tailor, D. G. Hall, Org. Lett. 2000, 2, 3715-3718;
21. b) B. B. Touré, H. R. Hoveyda, J. Tailor, A. Ulaczyk-Lesanko, D. G. Hall, Chem. Eur. J. 2003, 9, 466-474.
22. a) X. Gao, D. G. Hall, J. Am. Chem. Soc. 2003, 125, 9308-9309;
23. b) M. Deligny, F. Carreaux, B. Carboni, L. Toupet, G. Dujardin, Chem. Commun. 2003, 276-277.
24. For a recent review on the synthesis of substituted piperidines, see: P. M. Weintraub, J. S. Sabol, J. A. Kane, D. R. Borcherding, Tetrahedron 2003, 59, 2953-2989.
25. For early isolation and structure elucidation through synthetic and degradation studies (note that the originally postulated C4-C5 dehydro structure of palustrine was wrong, and later corrected to C3-C4 dehydro on the basis of references [8 a-c], see: a) P. Karrer, C. H. Eugster, Helv. Chim. Acta 1948, 31, 1062-1066;
26. b) C. Mayer, J. Trueb, J. Wilson, C. H. Eugster, Helv. Chim. Acta 1968, 51, 661;
27. c) C. H. Eugster, Heterocycles 1976, 4, 51-105;
28. d) P. Rüedi C. H. Eugster, Helv. Chim. Acta 1978, 61, 899-904;
29. e) C. Mayer, C. L. Green, W. Trueb, P. C. Wälchli, C. H. Eugster, Helv. Chim. Acta 1978, 61, 905-921;
30. f) P. C. Wälchli, G. Mukherjee-Müller, C. H. Eugster, Helv. Chim. Acta 1978, 61, 921-928.
31. For syntheses of palustrine alkaloids: racemic syntheses of the wrong structure of palustrine: a) M. Natsume, M. Ogawa, I. Yoda, M. Shiro, Chem. Pharm. Bull. 1984, 32, 812-814;
32. b) H. H. Wasserman, M. R. Leadbetter, I. E. Kopka, Tetrahedron Lett. 1984, 25, 2391-2394; synthesis of racemic palustrine and structure revision:
33. c) M. Natsume, M. Ogawa, Chem. Pharm. Bull. 1984, 32, 3789-3791; total synthesis of (-)-dihydropalustramic acid:
34. d) O. Muraoka, B.-Z. Zheng, K. Okumura, G. Tanabe, T. Momose, C. H. Eugster, J. Chem. Soc. Perkin Trans. 1 1996, 1567-1575; a prospective intermediate for the synthesis of (+)-palustrine:
35. e) Y. Hirai, J. Watanabe, T. Nozaki, H. Yokoyama, S. Yamaguchi, J. Org. Chem. 1997, 62, 776-777; total synthesis of (-)-methyl palustramate:
36. f) S. R. Angle, R. M. Henry, J. Org. Chem. 1998, 63, 7490-7497.
37. The use of Lewis acids to facilitate the reaction of acrylates was unsatisfactory due to the basic character of the heterodienes employed.
38. A. Waldner, Tetrahedron Lett. 1989, 30, 3061-3064.
39. Selected references: a) W. Wucherpfennig, Tetrahedron Lett. 1967, 3235; W. Wucherpfennig, Justus Liebigs Ann. Chem. 1971, 761, 16-27;
40. Selected references: a) W. Wucherpfennig, Tetrahedron Lett. 1967, 3235; W. Wucherpfennig, Justus Liebigs Ann. Chem. 1971, 761, 16-27;
41. b) W. L. Mock, R. M. Nugent, J. Org. Chem. 1978, 43, 3433-3434;
42. c) M. M. Rogic, D. Masilamani, J. Am. Chem. Soc. 1977, 99, 5219-5220;
43. d) S. M. Weinreb, R. R. Staib, Tetrahedron 1982, 38, 3087-3128;
44. e) R. S. Garigipati, J.A. Morton, S. M. Weinreb, Tetrahedron Lett. 1983, 24, 987-990.
45. See the Supporting Information for more experimental details and spectroscopic data on new compounds.
46. Careful control of pH was desirable as significant degradation was observed at lower pH.
47. 1,3 strain between the planar exocyclic amide group and the neighboring substituents in the "diequatorial" conformation: M. Natsume, M. Ogawa, Chem. Pharm. Bull. 1982, 30, 3442-3445, and references therein. In the case of compounds 7, the planar hydrazine can be considered isosteric to an acyl group.
48. 3-Boronoacrolein pinacolate is available in two steps from commercial 3,3′-diethoxypropyne (see ref. [4b]).
49. a) E. M. White, J. Am. Chem. Soc. 1955, 77, 6011-6014;
50. b) D. A. Evans, P. H. Carter, C. J. Dinsmore, J. C. Barrow, J. L. Katz, D. W. Kung, Tetrahedron Lett. 1997, 38, 4535-4538.
51. T. R. Bailey, R. S. Garigipati, J. A. Morton, S. M. Weinreb, J. Am. Chem. Soc. 1984, 106, 3240-3245.
52. 13C NMR spectra of 5.