Synthesis of highly functionalized 2,5-disubstituted pyrrolidines via an aza-Morita-Baylis-Hillman-type reaction

Tetrahedron

Volumn 66, Issue 33, 2010, Pages 6293-6299

  Kitulagoda, James E ^a   Palmelund, Anders ^a   Aggarwal, Varinder K ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 BENZYL 2 METHYL 5 (1 OXOBUT 2 EN 2 YL) PYRROLIDINE 1,2 DICARBOXYLATE; 1 BENZYL 2 METHYL 5 (3 OXOBUT 1 EN 2 YL) PYRROLIDINE 1,2 DICARBOXYLATE; 1 BENZYL 2 METHYL 5 (3 OXOPROP 1 EN 2 YL) PYRROLIDINE 1,2 DICARBOXYLATE; 1 BENZYL 2 METHYL 5 (5 OXOCYCLOPENT 1 EN 1 YL) PYRROLIDINE 1,2 DICARBOXYLATE; 1 BENZYL 2 METHYL 5 (6 OXOCYCLOHEX 1 ENYL) PYRROLIDINE 1,2 DICARBOXYLATE; BENZYL 2 [[(TERT BUTYLDIPHENYLSILYL)OXY]METHYL] 5 (6 OXOCYCLOHEX 1 EN 1 YL) PYRROLIDINE 1 CARBOXYLATE; DIBENZYL 5 (1 OXOBUT 2 EN 2 YL) PYRROLIDINE 1,2 DICARBOXYLATE; DIBENZYL 5 (3 OXOBUT 1 EN 2 YL) PYRROLIDINE 1,2 DICARBOXYLATE; DIBENZYL 5 (3 OXOPROP 1 EN 2 YL) PYRROLIDINE 1,2 DICARBOXYLATE; DIBENZYL 5 (5 OXOCYCLOPENT 1 EN 1 YL) PYRROLIDINE 1,2 DICARBOXYLATE; PYRROLIDINE DERIVATIVE; QUINUCLIDINE; UNCLASSIFIED DRUG;

ARTICLE; AZA MORITA BAYLIS HILLMAN REACTION; BAYLIS HILLMAN REACTION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; MICHAEL ADDITION; PRIORITY JOURNAL; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 77955660832     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.05.047     Document Type: Article

References (42)

1. J.K. Whitesell, and S.W. Felman J. Org. Chem. 42 1977 1663 1664
2. (b) T. Yamazaki, J.T. Welch, J.S. Plummer, and R. Gimi Tetrahedron Lett. 32 1991 4267 4270
3. (c) C. Genicot, and L. Ghosez Tetrahedron Lett. 33 1992 7357 7360
4. (d) Q. Zhang, R.M. Mohan, L. Cook, S. Kazanis, D. Peisach, B.M. Foxman, and B.B. Snider J. Org. Chem. 58 1993 7640 7651
5. (e) S. He, S.A. Kozmin, and V.H. Rawal J. Am. Chem. Soc. 122 2000 190 191
6. (f) T. Katsuki, and M. Yamaguchi Tetrahedron Lett. 26 1985 5807 5810
7. (g) Y. Kawanami, Y. Ito, T. Kitagawa, and Y. Taniguchi Tetrahedron Lett. 25 1984 857 860
8. (h) D.F. Taber, G.J. Gorski, L.M. Liable-Sands, and A.L. Rheingold Tetrahedron Lett. 38 1997 6317 6318
9. (i) B.H. Kim, H.B. Lee, J.K. Hwang, and Y.G. Kim Tetrahedron: Asymmetry 16 2005 1215 1220
10. (a) H. Chen, J.A. Sweet, K.-C. Lam, A.L. Rheingold, and D.V. McGrath Tetrahedron: Asymmetry 20 2009 1672 1682
11. (b) R. Hoen, M. van denBerg, H. Bernsmann, A.J. Minnaard, J.G. de Vries, and B.L. Feringa Org. Lett. 6 2004 1433 1436
12. (c) R. Stranne, and C. Moberg Eur. J. Org. Chem. 2001 2191 2195
13. N. Halland, A. Braunton, S. Bachmann, M. Marigo, and K.A. Jorgensen J. Am. Chem. Soc. 126 2004 4790 4791
14. (a) T. Shono, T. Fujita, and Y. Matsumura Chem. Lett. 1991 81 84
15. (b) V.K. Aggarwal, C.J. Astle, H. Iding, B. Wirz, and M. Rogers-Evans Tetrahedron Lett. 46 2005 945 947
16. (c) S. Asada, M. Kato, K. Asai, T. Ineyama, S. Nishi, K. Izawa, and T. Shono J. Chem. Soc., Chem. Commun. 1989 486 488
17. (d) R.A. Pilli, L.C. Dias, and A.O. Maldaner J. Org. Chem. 60 1995 717 722
18. (e) S.F. Martin, K.J. Barr, D.W. Smith, and S.K. Bur J. Am. Chem. Soc. 111 1999 6990 6997
19. M.V. Chiesa, L. Manzoni, and C. Scolastico Synlett 1996 441 443
20. (a) L.-G. Wistrand, and M. Skrinjar Tetrahedron 47 1991 573 582
21. (b) I. Collado, J. Ezquerra, and C. Pedregal J. Org. Chem. 60 1995 5011 5015
22. (a) E.J. Corey, P.-W.Y. Francis, F.J. Hannon, and D.A. Wierda J. Org. Chem. 55 1990 784 786
23. (b) G. Sunilkumar, D. Nagamani, N.P. Argade, and K.N. Ganesh Synthesis 2003 2304 2306
24. (c) J. Ahman, and P. Somfai Tetrahedron 48 1992 9537 9544
25. (d) T. Katoh, Y. Nagata, Y. Kobayashi, K. Arai, J. Minami, and S. Terashima Tetrahedron 50 1990 6221 6238
26. (e) N. Langlois, and Rojas Tetrahedron 49 1993 77 82
27. (f) N. Langlois, A. Rojas-Rousseau, and O. Decavallas Tetrahedron: Asymmetry 7 1996 1095 1100
28. (g) T. Katoh, Y. Nagata, Y. Kobayashi, K. Arai, J. Minami, and S. Terashima Tetrahedron Lett. 34 1993 5743 5746
29. Y. Matsumara, T. Kinoshita, Y. Yanagihara, N. Kanemoto, and M. Watanabe Tetrahedron Lett. 37 1996 8395 8398
30. (a) E.L. Myers, J.G. de Vries, and V.K. Aggarwal Angew. Chem., Int. Ed. 46 2007 1893 1896
31. (b) J.C. Killen, J. Leonard, and V.K. Aggarwal Synlett 2010 579 582
32. These conditions have been applied to the analogous Boc N,O-acetals, see Ref. 4b.
33. K. Lee, H. Kim, T. Miura, K. Kiyota, H. Kusama, S. Kim, N. Iwasawa, and P.H. Lee J. Am. Chem. Soc. 125 2003 9682 9688 See Ref. 9 for a related VT NMR study.
34. 2/TMSOTf were screened with temperatures ranging from -60°C to room temperature
35. S. Kim, Y.G. Kim, and J.H. Park Tetrahedron Lett. 32 1991 2043 2044
36. β-Phosphino silyl enol ethers are also known to be stable at room temperature, see: D.A. Evans, K.M. Hurst, and J.M. Takacs J. Am. Chem. Soc. 100 1978 3467 3477
37. See Supplementary data for the preparation of hemi-aminal 9c from which pyrrolidine 19 is derived.
38. For a discussion of the factors affecting diastereoselectivity in reactions of cyclic oxocarbenium ions see: D.M. Smith, and K.A. Woerpel Org. Biomol. Chem. 4 2006 1195 1201
39. (a) M. Oba, S. Koguchi, K. Nishiyama, D. Kaneno, and S. Tomoda Angew. Chem., Int. Ed. 43 2004 2412 2415
40. (b) A.G.M. Barrett, and D. Pilipauskas J. Org. Chem. 56 1991 2787 2800
41. J. Mulzer, F. Schülzchen, and J.-W. Bats Tetrahedron 56 2000 4289 4298
42. H. Dhimane, C. Vanucci-Bacque, L. Hamon, and G. Lhommet Eur. J. Org. Chem. 1998 1955 1963