Diastereoselective intermolecular [4 + 3] cycloadditions via an extended transition state: A route to enantiomerically enriched cycloadducts

Journal of the American Chemical Society

Volumn 118, Issue 44, 1996, Pages 10930-10931

  Lautens, Mark ^a   Aspiotis, Renee ^a   Colucci, John ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.2.1]OCTANE DERIVATIVE; FURAN DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; TECHNIQUE;

EID: 0029824320     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962460r     Document Type: Article

References (32)

1. For reviews on [4 + 3] cycloadditions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, Chapter 5.1, p 593. (b) Mann, J. Tetrahedron 1986, 42, 4611. (c) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163.
2. For reviews on [4 + 3] cycloadditions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, Chapter 5.1, p 593. (b) Mann, J. Tetrahedron 1986, 42, 4611. (c) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163.
3. For reviews on [4 + 3] cycloadditions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, Chapter 5.1, p 593. (b) Mann, J. Tetrahedron 1986, 42, 4611. (c) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163.
4. For reviews on [4 + 3] cycloadditions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, Chapter 5.1, p 593. (b) Mann, J. Tetrahedron 1986, 42, 4611. (c) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163.
5. Nucleophilic ring opening on oxabicyclo[3.2.1] systems: (a) Lautens, M.; Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. Soc. 1995, 117, 532. (b) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954. (c) Arjona, O.; de Dios, A.; Fernandez de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906 and references therein. (d) Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281. (e) Lautens, M.; Abd-El-Aziz, A. S.; Lough, A. J. Org. Chem. 1990, 55, 5305.
6. Nucleophilic ring opening on oxabicyclo[3.2.1] systems: (a) Lautens, M.; Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. Soc. 1995, 117, 532. (b) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954. (c) Arjona, O.; de Dios, A.; Fernandez de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906 and references therein. (d) Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281. (e) Lautens, M.; Abd-El-Aziz, A. S.; Lough, A. J. Org. Chem. 1990, 55, 5305.
7. Nucleophilic ring opening on oxabicyclo[3.2.1] systems: (a) Lautens, M.; Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. Soc. 1995, 117, 532. (b) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954. (c) Arjona, O.; de Dios, A.; Fernandez de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906 and references therein. (d) Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281. (e) Lautens, M.; Abd-El-Aziz, A. S.; Lough, A. J. Org. Chem. 1990, 55, 5305.
8. Nucleophilic ring opening on oxabicyclo[3.2.1] systems: (a) Lautens, M.; Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. Soc. 1995, 117, 532. (b) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954. (c) Arjona, O.; de Dios, A.; Fernandez de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906 and references therein. (d) Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281. (e) Lautens, M.; Abd-El-Aziz, A. S.; Lough, A. J. Org. Chem. 1990, 55, 5305.
9. Nucleophilic ring opening on oxabicyclo[3.2.1] systems: (a) Lautens, M.; Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. Soc. 1995, 117, 532. (b) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954. (c) Arjona, O.; de Dios, A.; Fernandez de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906 and references therein. (d) Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281. (e) Lautens, M.; Abd-El-Aziz, A. S.; Lough, A. J. Org. Chem. 1990, 55, 5305.
10. N2′ like" ring openings of oxa-n-cyclo systems, see: (a) Keay, B. A.; Woo, S. Synthesis 1996, 669. (b) Lautens, M. Synlett 1993, 177.
11. N2′ like" ring openings of oxa-n-cyclo systems, see: (a) Keay, B. A.; Woo, S. Synthesis 1996, 669. (b) Lautens, M. Synlett 1993, 177.
12. Lautens, M.; Klute, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 442.
13. For an alternative approach to enantiomerically enriched oxabicyclo-[3.2.1]octenes via a tandem cyclopropanation/Cope rearrangement, see: Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774.
14. For stereoselective intramolecular [4 + 3] cycloadditions, see: (a) Harmata, M.; Elomari, S.; Barnes, C. L. J. Am. Chem. Soc. 1996, 118, 2860. (b) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795.
15. For stereoselective intramolecular [4 + 3] cycloadditions, see: (a) Harmata, M.; Elomari, S.; Barnes, C. L. J. Am. Chem. Soc. 1996, 118, 2860. (b) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795.
16. For the kinetic resolution of 1b-d, see: (a) Kusakabe, M.; Kitano, Y.; Kobayashi, Y.; Sato, F. J. Org. Chem. 1989, 54, 2085. For the preparation of 1e and 2, see: (b) Schmid, C. R.; Bryant. J. D. In Organic Syntheses; Coffen, D. L., Ed.; Wiley: New York, 1993; Vol. 72, p 6. (c) Suzuki, K.; Yuki, Y.; Mukaiyama, T. Chem. Lett. 1981, 1529. (d) Sato, F.; Kobayashi, Y.; Takahashi, O.; Chiba, T.; Takeda, Y.; Kusakabe, M. J. Chem. Soc., Chem. Commun. 1985, 1636.
17. For the kinetic resolution of 1b-d, see: (a) Kusakabe, M.; Kitano, Y.; Kobayashi, Y.; Sato, F. J. Org. Chem. 1989, 54, 2085. For the preparation of 1e and 2, see: (b) Schmid, C. R.; Bryant. J. D. In Organic Syntheses; Coffen, D. L., Ed.; Wiley: New York, 1993; Vol. 72, p 6. (c) Suzuki, K.; Yuki, Y.; Mukaiyama, T. Chem. Lett. 1981, 1529. (d) Sato, F.; Kobayashi, Y.; Takahashi, O.; Chiba, T.; Takeda, Y.; Kusakabe, M. J. Chem. Soc., Chem. Commun. 1985, 1636.
18. For the kinetic resolution of 1b-d, see: (a) Kusakabe, M.; Kitano, Y.; Kobayashi, Y.; Sato, F. J. Org. Chem. 1989, 54, 2085. For the preparation of 1e and 2, see: (b) Schmid, C. R.; Bryant. J. D. In Organic Syntheses; Coffen, D. L., Ed.; Wiley: New York, 1993; Vol. 72, p 6. (c) Suzuki, K.; Yuki, Y.; Mukaiyama, T. Chem. Lett. 1981, 1529. (d) Sato, F.; Kobayashi, Y.; Takahashi, O.; Chiba, T.; Takeda, Y.; Kusakabe, M. J. Chem. Soc., Chem. Commun. 1985, 1636.
19. For the kinetic resolution of 1b-d, see: (a) Kusakabe, M.; Kitano, Y.; Kobayashi, Y.; Sato, F. J. Org. Chem. 1989, 54, 2085. For the preparation of 1e and 2, see: (b) Schmid, C. R.; Bryant. J. D. In Organic Syntheses; Coffen, D. L., Ed.; Wiley: New York, 1993; Vol. 72, p 6. (c) Suzuki, K.; Yuki, Y.; Mukaiyama, T. Chem. Lett. 1981, 1529. (d) Sato, F.; Kobayashi, Y.; Takahashi, O.; Chiba, T.; Takeda, Y.; Kusakabe, M. J. Chem. Soc., Chem. Commun. 1985, 1636.
20. 1H NMR analyses of the coupling constants. See: Hoffmann, H. M. R.; Clemens, K. E.; Smithers, R. H. J. Am. Chem. Soc. 1972, 94, 3940.
21. Noyori, R.; Sato, T. Bull. Chem. Soc. Jpn. 1978, 51, 2745.
22. 1′ hydroxyl respectively (NaH, THF, 0 °C then Mel).
23. 1′ hydroxyl.
24. 4.
25. X-ray crystallographic analyses of the major products resulting from 1e and 2, to be published by Lautens, M.; Colucci, J. T.; Lough, A. J.
26. (a) Mann, J.; Barbosa, L. C. A. J. Chem. Soc., Perkin Trans. I 1992, 787.
27. (b) Mann, J.; Barbosa L. C. A. Synthesis 1996, 31.
28. 2EDTA/EtOAc quench (1: 1).
29. 14b THF proved to be the best solvent for our cycloadditions. Furthermore, Mann observed predominant formation of diequatorial cycloadducts with 3-(2-furyl)propanol in benzene. Further investigations are required to determine why the diastereoselectivity changes as a function of the position of the hydroxyl group on the side chain.
30. A complex related to 17 may be invoked to explain the observed facial selectivity and stereoselectivity. Divalent zinc (or perhaps an aggregate containing zinc ions) may act as a tether between the furyl alkoxide and the oxyallyl cation. equation presented
31. 4, THF, 0 °C) proved the structure of the cycloadduct-unpublished results).
32. Lautens, M; Kumanovic, S.; Meyer, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1329.