Direct catalytic asymmetric vinylogous mannich-type and michael reactions of an α,β-unsaturated γ-butyrolactam under dinuclear nickel catalysis

Journal of the American Chemical Society

Volumn 132, Issue 11, 2010, Pages 3666-3667

  Shepherd, Nicholas E ^a   Tanabe, Hirookl ^a   Xu, Yingjie ^a   Matsunaga, Shlgekl ^a   Shlbasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; DINUCLEAR; MANNICH-TYPE REACTIONS; MICHAEL ADDUCTS; MICHAEL REACTIONS; NICKEL CATALYSIS; NITROALKENES; SCHIFF BASE COMPLEXES;

FUNCTIONAL GROUPS;

ADDITION REACTIONS;

2 PYRROLIDINONE; ALKENE DERIVATIVE; IMINE; NICKEL; SCHIFF BASE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MANNICH REACTION; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

ALKENES; CATALYSIS; LACTAMS; MAGNETIC RESONANCE SPECTROSCOPY; NICKEL; STEREOISOMERISM;

EID: 77949810865     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1002636     Document Type: Article

References (30)

1. Reviews: (a) Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G. Synlett 2009, 1525.
2. (b) Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929.
3. For selected examples of asymmetric vinylogous Mannich-type reactions of siloxyfurans, see: (a) Martin, S. F.; Lopez, O. D. Tetrahedron hatt. 1999, 40, 8949.
4. (b) Carswell, E. L.; Snapper, M. L.; Hovevda. A. H. Angew. Chem, Int. Ed. 2006, 45, 7230.
5. (c) Akiyama, T.; Honma, Y.; Itoh, J.; Fuchibe, K. adv. Synth. Catal. 2008, 350, 399.
6. (d) Mandai, H.; Mandai, K.; Snapper, M. L.; Hoveyda A. H. J. Am. Chem. Soc. 2008, 130, 17961.
7. (e) Salvador González, A.; Gomez Arrayás, R.; Rodríguez Rivero, M.; Carretero, J. C. Org. Lett. 2008, 10, 4335.
8. (f) Yuan, Z.-L.; Jiang, J.-J.; Shi, M. Tetraheron 2009, 65, 6001. For other examples, see ref 1.
9. For direct catalytic asymmetric vinylogous reaction of γ-butenolides, Mannich-type reaction: (a) Yamaguchi, A.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2008, 10, 2319. 1,4-Addition to nitroalkenes:
10. (b) Trost, B. M.; Hitce, J. J. Am. Chem. Soc. 2009, 131, 4572.
11. (a) DeGoey, D. A.; Chen, H.-J.; Flosi, W. J.; Grampovnik, D. J.; Yeung, C. M.; Klein, L. L.; Kempf, D. J. J. Org. Chem. 2002, 67, 5445.
12. (b) Barnes, D. M.; Bhagavatula, L.; DeMattei, J.; Gupta, A.; Hill, D. R.; Manna, S.; McLaughlin, M. A.; Nichols, P.; Premchandran, R.; Rasmussen, M. W.; Tian, Z.; Wittenberger, S. J. Tetrahedron: Asymmetry 2003, 14, 3541. For other synthetic applications and stereoselective transformation of α,βunsaturated γ-butyrolactam unit, see ref la.
13. Suga, H.; Takemoto, H.; Kakehi, A. Heterocycles 2007, 71, 361.
14. Curti, C.; Sartori, A.; Battistini, L.; Rassu, G.; Zanardi, F.; Casiraghi, G. Tetrahedron Lett. 2009, 50, 3428.
15. For racemic direct-type vinylogous reactions of α,β- unsaturated γbutyrolactam and related donors, see: (a) Sartori, A.; Curti, C.; Battistini, L.; Burreddu, P.; Rassu, G.; Pelosi, G.; Casiraghi, G.; Zanardi, F. Tetrahedron 2008, 64, 11697.
16. (b) Curti, G; Sartori, A.; Battistini, L.; Rassu, G.; Burreddu, P.; Zanardi, F.; Casiraghi, G. J. Org. Chem. 2008, 73, 5446. For related racemic transformations of isoindolmones, see:
17. (c) Lamblin, M.; Couture, A.; Deniau, E.; Grandclaudon, P. Org. Biomol. Chem. 2007, 5, 1466, and references therein.
18. Review: (a) Shibasaki, M.; Matsunaga, S.; Kumagai, N. Synlett 2008, 1583. For a catalyst developed for α-selective addition of dienolates in direct aldol process, see:
19. (b) Yamaguchi, A.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 10842
20. 21:
21. 2-1:
22. (c) Kato, Y.; Furutachi, M.;Chen,Z.;Mitsunuma, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 9168.
23. 2-1: (a) Chen, Z.; Morimoto, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 2170.
24. (b) Mouri, S.; Chen, Z.; Mitsunum, H.; Furutachi, M.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 1255.
25. For selected examples of related afunctional bimetallic Schiff base complexes in asymmetric catalysis, see: (a) Annamalai, V.; DiMauro, E. F.; Carroll, P. J.; Kozlowski, M. G J. Org. Chem. 2003, 68, 1973, and references therein.
26. (b) Yang, M.; Zhu, C.; Yuan, F.; Huang, Y.; Pan, Y. Org. Lett. 2005, 7, 1927.
27. (c) Hirahata, W.; Thomas, R. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2008, 130, 17658.
28. (d.) Mazet, G; Jacobson, E. N. Angew. Chem. Int. Fd. 2008. 47, 1762.
29. (e) Wu, B.; Gallucci, J. C.; Parquette, J. R.; Rajanbabu, T. V. Angew. Chem. Int. Fd. 2009, 48, 1126.
30. The relative and absolute configurations of 5a and 7b were unequivocally determined by X-ray crystallographic analysis. See Supporting Information.