Chemoselectivity in dirhodium(II) catalyzed reactions of diazoacetoacetates prepared from α,β-unsaturated ketones

Arkivoc

Volumn 2010, Issue 8, 2010, Pages 10-16

  Zhang, Yu ^a   Doyle, Michael P ^a  

^a Bldg 142   (United States)

Author keywords

Aromatic substitution; C H insertion; Mukaiyama Michael reaction; Rhodium acetate

Indexed keywords

EID: 77953406615     PISSN: 15517012     EISSN: 15517004     Source Type: None    
DOI: 10.3998/ark.5550190.0011.803     Document Type: Article

References (16)

1. Doyle, M. P.; Liu, Y; Zhang, Y; Jee, N. Org. Lett. 2008, 10, 1605.
2. (a) Calter, M. A.; Sugathapala, P., M.; Zhu, C. Tetrahedron Lett. 1997, 38, 3837.
3. (b) Calter, M. A.; Zhu, C. J. Org. Chem. 1999, 64, 1415.
4. (c) Deng, G.; Tian, X.; Qu, Z.; Wang, J. Angew. Chem. Int. Ed. 2002, 41, 2773.
5. Doyle, M. P.; Kundu, K.; Russell, A. E. Org. Lett. 2005, 7, 5171.
6. Kundu, K.; Doyle, M. P. Tetrahedron: Asymmetry 2006, 17, 574.
7. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; John Wiley & Sons: New York, 1998.
8. Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc. 1993, 115, 958.
9. (a) Taber, D. F.; Ruckle, R. E. Jr, J. Am. Chem. Soc. 1986, 108, 7686.
10. (b) Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547.
11. Hashimoto, S.; Watanabe, N.; Ikegami, S. Tetrahedron Lett. 1992, 33, 2709.
12. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2009, ASAP; DOI:10.1021/cr900239n.
13. Padwa, A.; Austin, D. J.; Hornbuckle, S. F.; Semones, M. A.; Doyle, M. P.; Protopopova, M. N. J. Am. Chem. Soc. 1993, 114, 1874.
14. Doyle, M. P.; Shanklin, M. S.; Pho, H. Q.; Mahapatro, S. N. J. Org. Chem. 1988, 53, 1017.
15. Doyle, M. P.; Mahapatro, S. N.; Guy, J. K.; Hester, M. R.; VanZyl, C. M.; Boundy, K. L. Inorg. Chem. 1987, 26, 3387.
16. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774.