Direct synthesis of fused, bicyclic γ-butyrolactones via tandem reductive cyclization-carbonylation of tethered enals and enones

Journal of the American Chemical Society

Volumn 118, Issue 6, 1996, Pages 1557-1558

  Crowe, William E ^a   Vu, An T ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CYCLOPENTANE DERIVATIVE;

ARTICLE; CRYSTALLOGRAPHY; CYCLIZATION; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029944796     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9535874     Document Type: Article

References (21)

1. Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94-110.
2. See, for example: (a) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y. S.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793-8794. (b) Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505-5506. (c) Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593-8601. (d) Bernardes, V.; Verdaguer, X.; Kardos, N.; Riera, A.; Moyano, A.; Pericas, M. A.; Greene, A. E. Tetrahedron Lett. 1994, 35, 575-578. (e) Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199-7207. (f) Schore, N. E. Org. React. (N.Y.) 1991, 40, 1-90. (g) Negishi, E.; Swanson, D. R., Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1987, 28, 917-920.
3. See, for example: (a) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y. S.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793-8794. (b) Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505-5506. (c) Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593-8601. (d) Bernardes, V.; Verdaguer, X.; Kardos, N.; Riera, A.; Moyano, A.; Pericas, M. A.; Greene, A. E. Tetrahedron Lett. 1994, 35, 575-578. (e) Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199-7207. (f) Schore, N. E. Org. React. (N.Y.) 1991, 40, 1-90. (g) Negishi, E.; Swanson, D. R., Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1987, 28, 917-920.
4. See, for example: (a) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y. S.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793-8794. (b) Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505-5506. (c) Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593-8601. (d) Bernardes, V.; Verdaguer, X.; Kardos, N.; Riera, A.; Moyano, A.; Pericas, M. A.; Greene, A. E. Tetrahedron Lett. 1994, 35, 575-578. (e) Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199-7207. (f) Schore, N. E. Org. React. (N.Y.) 1991, 40, 1-90. (g) Negishi, E.; Swanson, D. R., Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1987, 28, 917-920.
5. See, for example: (a) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y. S.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793-8794. (b) Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505-5506. (c) Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593-8601. (d) Bernardes, V.; Verdaguer, X.; Kardos, N.; Riera, A.; Moyano, A.; Pericas, M. A.; Greene, A. E. Tetrahedron Lett. 1994, 35, 575-578. (e) Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199-7207. (f) Schore, N. E. Org. React. (N.Y.) 1991, 40, 1-90. (g) Negishi, E.; Swanson, D. R., Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1987, 28, 917-920.
6. See, for example: (a) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y. S.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793-8794. (b) Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505-5506. (c) Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593-8601. (d) Bernardes, V.; Verdaguer, X.; Kardos, N.; Riera, A.; Moyano, A.; Pericas, M. A.; Greene, A. E. Tetrahedron Lett. 1994, 35, 575-578. (e) Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199-7207. (f) Schore, N. E. Org. React. (N.Y.) 1991, 40, 1-90. (g) Negishi, E.; Swanson, D. R., Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1987, 28, 917-920.
7. See, for example: (a) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y. S.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793-8794. (b) Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505-5506. (c) Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593-8601. (d) Bernardes, V.; Verdaguer, X.; Kardos, N.; Riera, A.; Moyano, A.; Pericas, M. A.; Greene, A. E. Tetrahedron Lett. 1994, 35, 575-578. (e) Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199-7207. (f) Schore, N. E. Org. React. (N.Y.) 1991, 40, 1-90. (g) Negishi, E.; Swanson, D. R., Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1987, 28, 917-920.
8. See, for example: (a) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y. S.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793-8794. (b) Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505-5506. (c) Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593-8601. (d) Bernardes, V.; Verdaguer, X.; Kardos, N.; Riera, A.; Moyano, A.; Pericas, M. A.; Greene, A. E. Tetrahedron Lett. 1994, 35, 575-578. (e) Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199-7207. (f) Schore, N. E. Org. React. (N.Y.) 1991, 40, 1-90. (g) Negishi, E.; Swanson, D. R., Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1987, 28, 917-920.
9. Mashima, K.; Haraguchi, H.; Oyoshi, A.; Sakai, N.; Takaya, H. Organometallics 1991, 10, 2731-2736.
10. Hewlett, D. F.; Whitby, R. J. J. Chem. Soc., Chem. Commun. 1990, 1684-1686.
11. (a) Kool, L. B.; Rausch, M. D.; Alt, H. G.; Herberhold, M.; Thewalt, U.; Wolf, B. Angew. Chem., Int. Ed. Engl. 1985, 24 , 394.
12. (b) Binger, P.; Müller, P.; Benn, R.; Rufinska, A.; Gabor, B.; Krüger, C.; Betz, P. Chem. Ber. 1989, 122, 1035.
13. Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787-6788.
14. Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785-6786.
15. 3, the complexes decomposed slightly during the course of data acquisition.
16. 3 there are an upfield signal at δ 0.3-0.4 and a downfield signal at δ 2.2-2.3. For bicyclic 1-oxa-5-titanacyclopentanes 1a-I, there are an upfield signal at δ 0.82-1.11 and a downfield signal at δ 2.85-2.99.
17. (b) Cohen, S. A.; Bercaw, J. E. Organometallics 1985, 4, 1006-1014.
18. 2 in 15 mL of pentane was added directly 98 mg (1 mmol) of 5-hexenal 1a. After being stirred for 2 h at room temperature, the reaction mixture was filtered through a pad of Celite and rinsed with pentane to give a reddish solution of metallacycle 2a. To this solution was introduced atmospheric pressure of carbon monoxide via a balloon at room temperature for an additional 12 h. The solution color changed from red to deep red-purple, indicating formation of 3a. After 20 mL of ethyl ether was added, the reaction mixture was exposed to air and stirred for 4 h, during which time it turned bright yellow and a precipitate formed. The resulting yellow mixture was filtered through a pad of silica gel, rinsed with 3:1 ether/pentane (2 × 40 mL). The filtrate was concentrated under reduced pressure to give a yellow liquid residue, which was chromatographed on silica gel using 5:1 hexanes/EtOAc as eluent to give the lactone product as a colorless liquid. Yield: 76.0 mg (60.3%).
19. -1).
20. 2 and, in low yield, the acyclic aldehyde (from 2j) or imine (from 2k.I) used to form the metallacycle substrate.
21. Preliminary studies indicate that replacing CO with more Lewis basic isonitriles results in a faster insertion followed by an unexpected rearrangement: W. E. Crowe, A. T. Vu, manuscript in preparation.