Highly regioselective copper-catalyzed cis- and trans-1-propenyl Grignard cleavage of hindered epoxides. Application in propionate synthesis

Journal of Organic Chemistry

Volumn 71, Issue 15, 2006, Pages 5826-5829

  Rodriguez, David ^a   Mulero, Marlenne ^a   Prieto, José A ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXY ALCOHOLS; GRIGNARD CLEAVAGE; REGIOSELECTIVITY; TRANS-1-PROPENYLMAGNESIUM BROMIDE;

BROMINE COMPOUNDS; CATALYSIS; COPPER; ISOMERS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

COPPER; EPOXIDE; PROPIONIC ACID;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CIS TRANS ISOMERISM; DIASTEREOISOMER; GRIGNARD REACTION; ISOMERIZATION; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

ALKENES; ALKYNES; CATALYSIS; COPPER; EPOXY COMPOUNDS; MOLECULAR STRUCTURE; PROPIONIC ACIDS; STEREOISOMERISM;

EID: 33746375700     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060833t     Document Type: Article

References (38)

1. (a) Wakefield, B. J. Organomagnesium Methods in Organic Synthesis; Academic Press: London, 1995.
2. (b) Handbook of Grignard Reagents; Silverman, G. S., Rakita, P. E., Eds.; Marcel Dekker: New York, 1996.
3. (c) Grignard Reagents: New Developments; Richey, H. G., Jr., Ed.; Wiley: New York, 1999.
4. Recent reviews: (a) Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302-4320.
5. (b) Shinokubo, H.; Oshima, K. Eur. J. Org. Chem. 2004, 2081-2091.
6. Recent applications: (a) Rottlander, M.; Boymond, L.; Berillon, L.; Lepretre, A.; Varchi, G.; Avolio, S.; Laaziri, H.; Queguiner, G.; Ricci, A.; Cahiez, G.; Knochel, P. Chemistry 2000, 6, 767-770.
7. (b) Scheiper, B.; Bonnekessel, M.; Krause, H.; Fuerstner, A. J. Org. Chem. 2004, 69, 3943-3949.
8. (c) Itami, K.; Higashi, S.; Mineno, M.; Yoshida, J. Org. Lett. 2005, 7, 1219-1222.
9. (d) Limmert, M. E.; Roy, A. H.; Hartwig, J. F. J. Org. Chem. 2005, 70, 9364-9370.
10. (a) Taber, D. F.; Green, J. H.; Geremia, J. M. J. Org. Chem. 1997, 62, 9342-9344.
11. (b) Hodgson, D. M.; Fleming, M. J.; Stanway, S. J. J. Am. Chem. Soc. 2004, 126, 12250-12251.
12. (c) Tanaka, T.; Hiramatsu, K.; Kobayashi, Y.; Ohno, H. Tetrahedron 2005, 61, 6726-6742.
13. (a) Martin, L. D.; Stille, J. K. J. Org. Chem. 1982, 47, 3630-3633.
14. (b) Tius, M. A.; Fauq, A. H. J. Org. Chem. 1983, 48, 4131-4132.
15. (c) Erdik, E. Tetrahedron 1984, 40, 641-657.
16. (d) Millar, J. G.; Underbill, E, W. J. Org. Chem. 1986, 51, 4726-4728.
17. (e) Pineschi, M. New J. Chem. 2004. 28, 657-665.
18. (a) Lipshutz, B. H.; Barton, J. C. J. Org. Chem. 1988, 53, 4495.
19. (b) Marshall, J. A. Chem. Rev. 1989, 89, 1503-1511.
20. (c) Lipshutz, B. H.; Barton, J. C. J. Am. Chem. Soc. 1992, 114, 1084-1086.
21. (d) Guanti, G.; Merlo, V.; Narisano, E. Tetrahedron 1994, 50, 12245-12258.
22. (e) Chauret, D. C.; Chong, J. M.; Ye, Q. Tetrahedron: Asymmetry 1999, 10, 3601-3614.
23. (a) Chini, M.; Crotti, P.; Flippin, L. A.; Gardelli, C.; Giovani, E.; Macchia, F.; Pineschi, M. J. Org. Chem. 1993, 58, 1221-1227.
24. (b) Sasaki, M.; Tanino, K.; Miyashita, M. J. Org. Chem. 2001, 66, 5388-5394.
25. (c) Pena, P. C. A.; Roberts, S. M. Curr. Org. Chem. 2003, 7, 555-571.
26. (d) Restorp, P.; Somfai, P. Chem. Commun. 2004, 2086-2087.
27. (e) Tirado, R.; Torres, G.; Torres, W.; Prieto, J. A. Tetrahedron Lett. 2005, 797-801.
28. (f) Lewinski, J.; Horeglad, P.; Tratkiewicz, E.; Justyniak, I.; Ochal, Z. J. Organomet. Chem. 2005, 690, 3697-3699.
29. Schlenk, W.; Schlenk, W., Jr. Her. Dtsch. Chem. Ges. 1929, 62, 920-924.
30. (a) Sarangi, C.; Das, N. B.; Nanda, B.; Nayak, A.; Sharma, R. P. J. Chem. Res. 1997, 180.
31. (b) Bonini, C.; Righi, G. Synlett 1992, 204-206.
32. Nicolaou, K. C.; Buggan, M. E.; Ladduwahetty, T. Tetrahedron Lett. 1984, 25, 2069.
33. All compounds were fully characterized by ID and 2D NMR (COSY and HMQC) methods. For known compound, the spectral data were compared with the literature values reported in refs 7e and 12.
34. (a) Tirado, R.; Prieto, J. A. J. Org. Chem. 1993, 58, 5666-5673.
35. (b) Torres, G.; Torres, W.; Prieto, J. A. Tetrahedron 2004, 60, 10245-10251.
36. (c) Arbelo, D. O.; Prieto, J. A. Tetrahedron Lett. 2002, 43, 4111-4114.
37. Beak, P.; Yamamoto, J.; Upton, C. J. J. Org. Chem. 1975, 40, 3052-3062.
38. Epoxide 26 was prepared from epoxide 1 by the corresponding alkynyl alane methodology (refs 12a,b).