Direct asymmetric michael addition to nitroalkenes: Vinylogous nucleophilicity under dinuclear zinc catalysis

Journal of the American Chemical Society

Volumn 131, Issue 13, 2009, Pages 4572-4573

  Trost, Barry M ^a   Hitce, Julien ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2(5H)-FURANONE; CONJUGATE ADDITION; DIASTEREO- AND ENANTIOSELECTIVITY; DINUCLEAR; GOOD YIELD; MICHAEL ADDITIONS; MICHAEL ADDUCTS; NITROALKENES; NUCLEOPHILICITY;

ADDITION REACTIONS; ENANTIOSELECTIVITY; STEREOSELECTIVITY; ZINC;

CATALYSIS;

ALKENE DERIVATIVE; NITROALKENE DERIVATIVE; UNCLASSIFIED DRUG; ZINC COMPLEX; ALKENE; GAMMA BUTYROLACTONE; LACTONE; NITRO DERIVATIVE; ZINC;

ALKYLATION; ARTICLE; CATALYSIS; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; STEREOCHEMISTRY; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

4-BUTYROLACTONE; ALKENES; CATALYSIS; LACTONES; NITRO COMPOUNDS; STEREOISOMERISM; ZINC;

EID: 67949100393     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja809723u     Document Type: Article

References (32)

1. Recent review: Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701.
2. Reviews: (a) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
3. (b) Christoffers, J.; Koripelly, G.; Rosiak, A.; Rössle, M. Synthesis 2007, 1279. Selected examples involving nitroalkenes as acceptors: Barnes, D. M.; Ji, J.; Fickes, M. G.; Fitzgerald, M. A.; King, S. A.; Morton, H. E.; Plagge, F. A.; Preskill, M.; Wagaw, S. H.; Wittenberger, S. J.; Zang, J. J. Am. Chem. Soc. 2002, 124, 13097.
4. (d) Watanabe, M.; Ikagawa, A.; Wang, H.; Murata, K.; Ikariya, T. J. Am. Chem. Soc. 2004, 126, 11148.
5. (e) Lu, S.-F.; Du, D.-M.; Xu, J.; Zhang, S.-W. J. Am. Chem. Soc. 2006, 128, 7418.
6. (f) Evans, D. A.; Mito, S.; Seidel, D. J. Am. Chem. Soc. 2007, 129, 11583.
7. (3)
8. (a) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003.
9. (b) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367.
10. (c) Xiao, Y.; Wang, Z.; Ding, K. Chem.-Eur. J. 2005, 11, 3668. For the effects of additional ligation, see :
11. (d) Trost, B. M.; Fettes, A.; Shireman, B. T. J. Am. Chem. Soc. 2004, 126, 2660.
12. The use of self-assembled multimetallic chiral catalysts was pioneered by Shibasaki: (a) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194.
13. (b) Shibasaki, M. Pure Appl. Chem. 1996, 68, 523.
14. Latest examples: (a) Trost, B. M.; Müller, C. J. Am. Chem. Soc. 2008, 130, 2438.
15. (b) Trost, B. M.; Malhotra, S.; Mino, T.; Rajapaksa, N. S. Chem.-Eur. J. 2008, 14, 7648.
16. (c) Trost, B. M.; O'Boyle, B. J. Am. Chem. Soc. 2008, 130, 16190.
17. Fuson, R. Chem. Rev. 1935, 16, 1.
18. (a) Xue, D.; Chen, Y.-C.; Wang, Q.-W.; Cun, L.-F.; Zhu, J.; Deng, J.-G. Org. Lett. 2005, 7, 5293.
19. (b) Jiang, L.; Zheng, H.-T.; Liu, T.-Y.; Yue, L.; Chen, Y.-C. Tetrahedron 2007, 63, 5123.
20. For conjugate additions of 2-siloxyfuran, only R, β-unsaturated acyloxazolidin- 2-ones have been used as acceptors. Review: (a) Casiraghi, G.; Rassu, G. Synthesis 1995, 607;Selected examples: Szlosek, M.; Figade're, B. Angew. Chem., Int. Ed. 2000, 39, 1799.
21. (c) Desimoni, G.; Faita, G.; Filippone, S.; Mella, M.; Zampori, M. G.; Zema, M. Tetrahedron 2001, 57, 10203.
22. (d) Onitsuka, S.; Matsuoka, Y.; Irie, R.; Katsuki, T. Chem. Lett. 2003, 32, 974.
23. (e) Carswell, E. L.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2006, 45, 7230.
24. (f) Salvador Gonza'lez, A.; Go'mez Arraya's, R.; RodrI'guez Rivero, M.; Carretero, J. C. Org. Lett. 2008, 10, 4335.
25. During the course of this work, Shibasaki et al. reported their studies on a related 1,2-addition, highlighting the challenges associated with the direct use of γ-butenolides as nucleophiles: Yamaguchi, A.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2008, 10, 2319.
26. Examples of polynuclear zinc complexes featuring bridging bidentate ligands: (a) Uhlenbrock, S.; Wegner, R.; Krebs, B. J. Chem. Soc., Dalton Trans. 1996, 3731.
27. (b) Sakiyama, H.; Mochizuki, R; Sugawara, A.; Sakamoto, M; Nishida, Y; Yamasaki, M. J. Chem. Soc., Dalton Trans. 1999, 997.
28. Shing, T. K. M.; Tam, E. K. W.; Tai, V. W.-F.; Chung, I. H. F.; Jiang, Q. Chem.-Eur. J. 1996, 2, 50.
29. The stereochemistry of diol 5 was established by X-ray analysis.
30. (a) Chaveriat, L.; Stasik, I.; Demailly, G.; Beaupe're, D. Tetrahedron 2004, 60, 2079.
31. (b) Gireaud, L.; Chaveriat, L.; Stasik, I.; Wadouachi, A.; Beaupe're, D. Tetrahedron 2006, 62, 7455.
32. At the present time, this study has been limited to 2(5H)-furanone 2 as the nucleophile.