Tunable and highly regio- and diastereoselective vinylogous Mannich-type reaction of dioxinone-derived silyl dienolate

Journal of Organic Chemistry

Volumn 74, Issue 15, 2009, Pages 5754-5757

  Gu, Chun Ling ^a   Liu, Li ^a   Wang, Dong ^a   Chen, Yong Jun ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

COUNTERION; DIASTEREOMERS; DIASTEREOSELECTIVE; DIASTEREOSELECTIVITIES; FACILE ACCESS; LEWIS ACID CATALYSTS; MANNICH-TYPE REACTIONS; REGIOISOMER;

ESTERS; SILANES; SILVER COMPOUNDS;

STEREOSELECTIVITY;

ALKADIENE; LEWIS ACID; SILANE DERIVATIVE; SILVER; SODIUM PEROXIDE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; MANNICH REACTION; STEREOCHEMISTRY;

ACIDS; CATALYSIS; DIOXANES; ESTERS; MOLECULAR STRUCTURE; SILVER; STEREOISOMERISM;

EID: 68049115646     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900977y     Document Type: Article

References (47)

1. For examples for amino acid synthesis, see: (a) Drury, W. J. III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006-11007.
2. (b) Elder, A. M.; Rich, D. H. Org. Lett. 1999, 1, 1443-1446.
3. (c) Sabby, S.; Fang, X.; Gathergood, N.; Joergensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116.
4. (d) Saaby, S.; Bayon, P.; Aburel, P. S.; Joergensen, K. A. J. Org. Chem. 2002, 67, 4352-4361.
5. (e) Juhl, K.; Gathergood, N.; Joergensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995-2997.
6. (f) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F. III J. Am. Chem. Soc. 2002, 124, 1842-1843.
7. (g) Chowdari, N. S.; Suri, J. T.; Barbas, C. F. III Org. Lett. 2004, 6, 2507-2510.
8. For selected examples, see: (a) Jacobsen, M. F.; Skrydstrup, T. J. Org. Chem. 2003, 68, 7112-7114.
9. (b) Saaby, S.; Nakama, K.; Lie, M. A.; Hazell, R. G.; Joergensen, K. A. Chem. - Eur. J. 2003, 9, 6145-6154.
10. (c) Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10-17.
11. (d) Andreassen, T.; Haland, T.; Hansenb, L. K.; Gautun, O. R. Tetrahedron Lett. 2007, 48, 8413-8415.
12. Denmark, S. E.; Heemstra, J. R., Jr.; Beutner, G. L. Angew. Chem., Int. Ed. 2005, 44, 4682-4698 and references cited therein.
13. (a) Kawecki, R. Tetrahedron 2001, 57, 8385-8390.
14. (b) Villano, R.; Acocella, M. R.; Massa, A.; Palombi, L.; Scettri, A. Tetrahedron 2007, 63, 12317-12323.
15. For selected examples for vinylogous Mannich reaction of silyl dienolates, see: (c) Sickert, M.; Schneider, C. Angew. Chem., Int. Ed. 2008, 47, 3631-3634.
16. (d) Wieland, L. C.; Vieira, E. M.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 570-576.
17. (e) González, A. S.; Arrayás, R. G.; Rivero, M. R.; Carretero, J. Org. Lett. 2008, 10, 4335-4337.
18. (f) Martin, S. F. Acc. Chem. Res. 2002, 35, 895-904 and references cited therein.
19. (a) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106-2112.
20. (b) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169-3171.
21. (c) Davis, F. A.; Chao, B. Org. Lett. 2000, 2, 2623-2625.
22. (d) Davis, F. A.; Zhang, Y.; Anilkumar, G. J. Org. Chem. 2003, 68, 8061-8064.
23. (e) Davis, F. A.; Zhang, J.; Li, Y.; Xu, H.; DeBrosse, C. J. Org. Chem. 2005, 70, 5413-5419.
24. (a) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley: New York, 1997.
25. (b) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991-8035.
26. (c) Magriotis, P. A. Angew. Chem., Int. Ed. 2001, 40, 4377-4379.
27. (d) Ma, J.-A. Angew. Chem., Int. Ed. 2003, 42, 4290-4299.
28. (e) Sewald, N. Angew. Chem., Int. Ed. 2003, 42, 5794-5795.
29. (f) Hamashima, Y.; Sasamoto, N.; Hotta, D.; Somei, H.; Umebayashi, N.; Sodeoka, M. Angew. Chem., Int. Ed. 2005, 44, 1525-1529.
30. (a) Vu, V. A.; Bérillon, L.; Knochel, P. Tetrahedron Lett. 2001, 42, 6847-6850.
31. (b) Thibonnet, J.; Vu, V. A.; Bérillon, L.; Knochel, P. Tetrahedron 2002, 58, 4787-4800.
32. (c) Wang, X.-J.; Sun, X.-F.; Zhang, L.; Xu, Y.-B.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2006, 8, 305-307.
33. (a) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995.
34. (b) Morton, D.; Stockman, R. A. Tetrahedron 2006, 62, 8869-8905.
35. (c) Gragg, R.; McCaffrey, S.; Sridharan, V.; Fishwick, C. W. G.; Kilner, C.; Korn, S.; Bailey, K.; Blacker, J. Tertrahedron 2006, 62, 12159-12171.
36. (d) Dai, H.-X.; Lu, X.- Y. Org. Lett. 2007, 9, 3077-3080.
37. (e) Andreassen, T.; Hansen, L.-K.; Gauntun, O. R. Eur. J. Org. Chem. 2008, 4871-4876.
38. (f) Lin, G.-Q.; Xu, M.-H.; Zhong, Y.-W.; Sun, X.-W. Acc. Chem. Res., 2008, 41, 831-840 and references cited therein.
39. Yanagisawa, A.; Touge, T.; Arai, T. Angew. Chem., Int. Ed. 2005, 44, 1546-1548.
40. Beenen, M. A.; Weix, D. J.; Ellman, J. A. J. Am. Chem. Soc. 2006, 128, 6304-6305.
41. (a) De Lucca, G. V. Bioorg. Med. Chem. Lett. 1997, 7, 501-504.
42. (b) Chung, J. Y. L.; Hughes, D. L.; Zhao, D.; Song, Z.; Mathre, D. J.; Ho, G.-J.; McNamara, J. M.; Douglas, A. W.; Reamer, R. A.; Tsay, F.-R.; Varsolona, R.; McCauley, J.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1996, 61, 215-222.
43. (c) MacKenzie, A. R.; Marchington, A. P.; Middleton, D. S.; Newman, S. D.; Jones, B. C. J. Med. Chem. 2002, 45, 5365-5377.
44. (d) Schafmeister, C. E.; Brown, Z. Z.; Gupta, S. Acc. Chem. Res. 2008, 41, 1387-1398.
45. Marin, J.; Didierjean, C.; Aubry, A.; Casimir, J.-R.; Briand, J.-P. G.; Guichard, J. J. Org. Chem. 2004, 69, 130-141.
46. - (0.256 nm): Sunderrajan, S.; Freeman, B. D.; Hall, C. K. Ind. Eng. Chem. Res. 1999, 38, 4051-4059.
47. Naodovic, M.; Yamamoto, H. Chem. Rev. 2008, 108, 3132-3148.