Direct asymmetrie allylic alkylation of butenolides with morita-baylis-hillman carbonates

Organic Letters

Volumn 12, Issue 4, 2010, Pages 720-723

  Cui, Hai Lei ^a   Huang, Ji Rong ^a   Lei, Jie ^a   Wang, Zhao Feng ^a   Chen, Shi ^a   Wu, L I ^a   Chen, Ying Chun ^a,b  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

^b SICHUAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BUTENOLIDE; CARBONIC ACID DERIVATIVE; CINCHONA ALKALOID; DRUG DERIVATIVE; GAMMA BUTYROLACTONE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

4-BUTYROLACTONE; ALKYLATION; ALLYL COMPOUNDS; CARBONATES; CATALYSIS; CINCHONA ALKALOIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 76849100414     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100014m     Document Type: Article

References (57)

1. for a review on natural products containing the butenolide unit, see: (a) Alali F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504. For reviews on the synthesis of butenolides, see:
2. (b) Rao, Y. S. Chem. Rev. 1964, 64, 353.
3. (c) Negishi, E.; Kotora, M.Tetahedron 1997, 53, 6707.
4. (d) Montagnon, T.; Tofi, M.; Vassilikogiannakis, G. Acc. Chem. Res. 2008, 41, 1001.
5. For selected examples, see: (a) Movassaghi, M.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2456.
6. (b) Adrio, J.; Carretero, J. C. J. Am. Chem. Soc. 2007, 129, 778.
7. (c) He, Y.-T.; Yang, H.-N.; Yao, Z.-J. Tetrahedron 2002, 58, 8805.
8. (d) Jauch, J. Eur. Org. Chem. 2001, 473.
9. (e) Grossmann, G.; Poncioni, M.; Bornand, M.; Jolivet, B.; Neuburger, M.; Séquin, U. Tetrahedron 2003, 59, 3237.
10. (f) Patil, S. N.; Liu, F. J. Org. Chem. 2008, 73, 4476.
11. For reviews, see: (a) Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929.
12. (b) Denmark, S. E.; Heemstra, J. R., Jr.; Beutner, G. L. Angew. Chem. Int. Ed. 2005, 44, 4682.
13. (a) Yamaguchi, A.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2008, 10, 2319.
14. (b) Trost, B. M.; Hitce, J. J. Am. Chem. Soc. 2009, 131, 4572.
15. Hyde, A. M.; Buchwald, S. L. Org. Lett. 2009, 11, 2663.
16. For catalytic asymmetric synthesis of γ,γ-disubstituted butenolides, see: (a) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192.
17. (b) Shaw, S. A.; Aleman, P.; Christy, J.; Kampf, J. W.; Va, P.; Vedejs, E. J. Am. Chem. Soc. 2006, 128, 925.
18. (a) Kim, J. N.; Lee, H. J.; Gong, J. H. Tetrahedron Lett. 2002, 43, 9141.
19. (b) Cho, C.-W.; Kong, J.-R.; Krische, M. J. Org. Lett. 2004, 6, 1337.
20. (c) Du, Y.; Han, X; Lu, X. Tetrahedron Lett. 2004, 45, 4967.
21. (d) Zhang, T.-Z.; Dai, L.-X.; Hou, X.-L. Tetrahedron: Asymmetry 2007, 18, 1990.
22. (e) van Steenis, D. J. V. C.; Marcelli, T.; Lutz, M.; Spek, A. L.; van Maarseveen, J. H.; Hiemstra, H. Adv. Synth. Catal. 2007, 349, 281.
23. (f) Park, H.; Cho, C.-W.; Krische, M. J. J. Org. Chem. 2006, 71, 7892.
24. (g) Ma, G.-N.; Cao, S.-H.; Shi, M. Tetrahedron: Asymmetry 2009, 20, 1086.
25. For studies from this group, see: (a) Cui, H.-L.; Peng, J.; Feng, X.; Du, W.; Jiang, K.; Chen, Y.-C. Chem.-Eur. J. 2009, 15, 1574.
26. (b) Jiang, K.; Peng, J.; Cui, H.-L.; Chen, Y.-C. Chem. Commun. 2009, 3955.
27. (c) Cui, H.-.L.; Feng, X.; Peng, J.; Jiang, K.; Chen, Y.-C. Angew. Chem. Int. Ed. 2009, 48, 5737.
28. (d) Feng, X.; Yuan, Y.-Q.; Cui, H.-L.; Jiang, K.; Chen, Y.-C. Org. Biomol. Chem. 2009, 7, 3660.
29. (e) Zhang, S.-J.; Cui, H.-L.; Jiang, K.; Li, R.; Ding, Z.-Y.; Chen, Y.-C. Eur. J. Org. Chem. 2009, 5804.
30. (a) Cho, C.-W.; Krische, M. J. Angew. Chem. Int. Ed. 2004, 43, 6689.
31. (b) Jiang, Y.-Q.; Shi, Y.-L.; Shi, M. J. Am. Chem. Soc. 2008, 130, 7202.
32. For reviews on the construction of a quaternary carbon center, see: (a) Christoffers, J.; Baro, A. Adv. Synth. Catal. 2005, 347, 1473.
33. (b) Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2007, 5969.
34. (c) Bella, M.; Gasperi, T. Synthesis 2009, 1583.
35. For selected examples of the construction of adjacent quaternary and tertiary chiral centers, see: (a) Austin, J. F.; Kim, S.-G.; Sinz, C. J.; Xiao, W.-J.; MacMillan, D. W. C. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5482.
36. (b) Li, H.; Wang, Y.; Tang, L.; Wu, F.; Liu, X.; Guo, C.; Foxman, B. M.; Deng, L. Angew. Chem. Int. Ed. 2005, 44, 105.
37. (c) Trost, B. M.; Zhang, Y. J. Am. Chem. Soc. 2007, 129, 14548.
38. (d) Wilt, J. C.; Pink, M.; Johnston, J. N. Chem. Commun. 2008, 4177.
39. (e) Bui, T.; Syed, S.; Barbas, C F., III J. Am. Chem. Soc. 2009, 131, 8758.
40. (f) Kato, Y.; Furutachi, M.; Chen, Z.; Mitsunuma, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 9168.
41. 1H NMR analysis. Excellent diastereoselectivities (generally >95:5) were reported in the similar reaction of 2-silyloxyfuran by Krische and Shi; see ref 9.
42. For reviews, see: (a) Tian, S.-K.; Chen, Y.; Hang, J.; Tang, L.; McDaid, P.; Deng, L. Acc. Chem. Res. 2004, 37, 621.
43. (b) Gaunt, M. J.; Johansson, C. C. C. Chem. Rev. 2007, 107, 5596.
44. The obtained stereochemistry is consistent with that observed when catalysis by triphenylphosphine is employed; see ref 9a.
45. For examples with .related frameworks, see: (a) Lemire, A.; Charette, A. B. Org. Lett. 2005, 7, 2747.
46. (b) Cassidy, M. P.; Padwa, A. Org. Lett. 2004, 6, 4029.
47. (c) Wee, A. G. H.; Fan, G.-J. Org. Lett. 2008, 10, 3869.
48. (d) Heretsch, P.; Rabe, S.; Giannis, A. Org. Lett. 2009, 11, 5410.
49. For examples with related frameworks, see: (a) Fuchs, S.; Berl, V.; Lepoittevin, J.-P. Eur. J. Org. Chem. 2007, 1145.
50. (b) Maulide, N.; Marko, I. E. Chem. Commun. 2006, 1200.
51. (c) Zhang, W.; Romo, D. ¿- J. Org. Chem. 2007, 72, 8939.
52. (d) Huber, R. S.; Jones, G. B. ¿¿J. Org. Chem. 1992, 57, 5778.
53. Enholm, E. J.; Kinter, K. S. J. Org. Chem. 1995, 60, 4850.
54. For examples with related frameworks, see: (a) Nobitec, E.; Aniol, M.; Wawrzeñczyk, C. Tetrahedron 1994, 50, 10339.
55. (b) Ghosh, A. K.; Takayama, J. Tetrahedron Lett. 2008, 49, 3409.
56. (c) Tello-Aburto, R.; Rios, M. Y.; Swenson, D. C.; Olivo, H. F. Terahedron Lett. 2008, 49, 6853.
57. (d) Brandvold, T. A.; Wulff, W. D.; Rheingold, A. L. ¿J. Am. Chem. Soc. 1990, 112, 1645.