Preparation of 5-hydroxycyclopentenones via conjugate addition-initiated nazarov cyclization

Organic Syntheses

Volumn 91, Issue , 2014, Pages 93-105

  Brooks, Joshua L ^a   Huang, Yu Wen ^a   Frontier, Alison J ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84896978750     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.091.0093     Document Type: Article

References (16)

1. Department of Chemistry, University of Rochester, Rochester, NY 14627, email frontier@chem.rochester.edu. This project has been supported by the NIGMS (R01 GM079364).
2. Huddleston, R. R.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 11488-11489.
3. Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4664-4668.
4. Riley, H. A.; Gray, A. R. Org. Synth. 1935, 15, 67.
5. Boeckman, R. K.; Shao, P.; Mullins, J. J. Org. Synth. 2000, 77, 141.
6. Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537.
7. Pellissier, H. Tetrahedron 2005, 61, 6479-6517.
8. Frontier, A. J.; Collison, C. Tetrahedron 2005, 61, 7577-7606.
9. Tius, M. A. Eur. J. Org. Chem. 2005, 2005, 2193-2206.
10. Grant, T. N.; Rieder, C. J.; West, F. G. Chem. Commun. 2009, 5676-5688.
11. Nakanishi, W.; West, F. G. Curr. Opin. Drug Discov. Devel. 2009, 12, 732-751.
12. Vaidya, T.; Eisenberg, R.; Frontier, A. J. Chem Cat Chem 2011, 3, 1531-1548.
13. Brooks, J. L.; Caruana, P. A.; Frontier, A. J. J. Am. Chem. Soc. 2011, 133, 12454-12457.
14. Brooks, J. L.; Frontier, A. J. J. Am. Chem. Soc. 2012, 134, 16551-16553.
15. The Krische protocol can only be employed in couplings with aryl glyoxals or non-enolizable aliphatic glyoxals, because alphatic glyoxals with 〈-protons polymerize rapidly (Riley, H. L.; Morley, J. F.; Friend, N. A. C. J. Chem. Soc. 1932, 1875-1883). Therefore, a different synthetic strategy must be used to prepare dienyl diketones like 5 (see reference 6).
16. Byproducts resulting from oxidative cleavage were observed in oxidation experiments using the Dess-Martin reagent, Jones reagent and MnO2, while decomposition was observed when TEMPO, TPAP-NMO, and Bi(NO3)3 were tested.