A Readily Synthesized and Highly Active Epoxide Carbonylation Catalyst Based on a Chromium Porphyrin Framework: Expanding the Range of Available β-Lactones

Organic Letters

Volumn 6, Issue 3, 2004, Pages 373-376

  Schmidt, Joseph A R ^a   Mahadevan, Viswanath ^a   Getzler, Yutan D Y L ^a   Coates, Geoffrey W ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; CHROMIUM DERIVATIVE; CHROMIUM PORPHYRIN; COBALT DERIVATIVE; EPOXIDE; HYDROCARBON; LACTONE DERIVATIVE; METAL; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; COMMERCIAL PHENOMENA; COMPLEX FORMATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 1342285527     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036244g     Document Type: Article

References (24)

1. For a review of β-lactone reactivity see: Pommier, A.; Pons, J. M. Synthesis 1993, 441-459.
2. Goodman, S. N.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 4703-4705.
3. Rieth, L. R.; Moore, D. R.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 15239-15248.
4. Yang, H. W.; Romo, D. Tetrahedron 1999, 55, 6403-6434.
5. Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936-938.
6. Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307-1315.
7. Drent, E.; Kragtwijk, E. Shell Internationale Research Maatschappij B. V., Netherlands, European Patent Application EP 577206; Chem. Abstr. 1994, 120, 191517c.
8. Lee, J. T.; Thomas, P. J.; Alper, H. J. Org. Chem. 2001, 66, 5424-5426.
9. Getzler, Y. D. Y. L.; Mahadevan, V.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 1174-1175 and references therein.
10. Mahadevan, V.; Getzler, Y. D. Y. L.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2781-2784 and references therein.
11. Davoli, P.; Moretti, I.; Prati, F.; Alper, H. J. Org. Chem. 1999, 64, 518-521.
12. Roe, D. C. Organometallics 1987, 6, 942-946.
13. Molnar, F.; Luinstra, G. A.; Allmendinger, M.; Rieger, B. Chem. Eur. J. 2003, 9, 1273-1280.
14. Allmendinger, M.; Eberhardt, R.; Luinstra, G. A.; Molnar, F.; Rieger, B. Z. Anorg. Allg. Chem. 2003, 629, 1347-1352.
15. TPP = 5,10,15,20-tetraphenylporphyrin.
16. Despite repeated crystallization attempts, crystals of X-ray quality proved elusive for catalyst 1.
17. -1) when employing conditions of 105°C and 60 bar of CO, although lactone selectivity in these reactions is limited to 91%, see ref 14.
18. Due to differences in heat flow and reactor volume, catalyst activity comparisons are less reliable when data from multiple high-pressure reactors are used. For this reason, all reactions detailed in this report were performed in a single reactor.
19. Pommier, A.; Pons, J. M. Synthesis 1995, 729-744.
20. For a review of carbocyclic eight-membered rings see: Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757-5821.
21. Adam, W.; Baeza, J.; Liu, J. J. Am. Chem. Soc. 1972, 94, 2000-2006.
22. Noyce, D. S.; Banitt, E. H. J. Org. Chem. 1966, 31, 4043-4047.
23. Cope, A. C.; Howell, C. F.; Bowers, J.; Lord, R. C.; Whitesides, G. M. J. Am. Chem. Soc. 1967, 89, 4024-4027.
24. One trans-and two cis-lactone isomers are produced upon carbonylation of cyclododecatriene monoxide (see the Supporting Information).