Stereoselectivity of Organometallic Reagents Addition to 7-Oxabicyclo[2.2.1]hept-5-en-2-one

Journal of Organic Chemistry

Volumn 54, Issue 17, 1989, Pages 4158-4164

  Arjona, Odön ^a   De La Pradilla, Roberto Fernández ^b   Mallo, Araceli ^a   Pérez, Sonia ^a   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000361392     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00278a032     Document Type: Article

References (29)

1. For a preliminary communication, see: Arjona, O.; Fernandez de la Pradilla, R.; Manzano, C.; Perez, S.; Plumet, J. Tetrahedron Lett. 1987, 28. 5547.
2. For a recent review, see: Lipshutz, B. H. Chem. Rev. 1986, 86, 795.
3. For some leading references, see: (a) Das, J.; Vu, T.; Harris, D. N.; Ogletree, M. L. J. Med. Chem. 1988, 31, 930. (b) Wilson, N. L.; Jones, R. L.; Marr, C. G.; Muir, G. Eur. J. Med. Chem. 1988, 23, 359. (c) Novak, B. M.; Grubbs, R. H. J. Am. Chem. Soc. 1988, 110, 960. (d) Jung, M. E.; Street, L. J. Heterocycles 1988, 27, 45. (e) Reymond, J. L.; Vogel, P. Tetrahedron Lett. 1988, 29, 3695. (f) Murai, A.; Tanimoto, N.; Sakamoto, N.; Masamune, T. J. Am. Chem. Soc. 1988, 110, 1985.
4. For a short synthesis of L-daunosamine, see: Warm, A.; Vogel, P. J. Org. Chem. 1986, 51, 5348. (b) For a synthesis of (+)- and (-)-methyl nonactate, see: Warm, A.; Vogel, P. Helv. Chim. Acta 1987, 70, 690. (c) For a synthesis of D- and L-ribose derivatives, see: Wagner, J.; Vieira, E.; Vogel, P. Helv. Chim. Acta 1988, 70, 624. (d) For a synthesis of (±)-castanospermine, see: Reymond, J. L.; Vogel, P. Tetrahedron Lett. 1989, 30. 705.
5. Vieira, E.; Vogel, P. Helv. Chim. Acta 1982, 65, 1700. (b) Moore, J. A.; Partain, E. J. Org. Chem. 1983, 48, 1105. (c) Brion, F. Tetrahedron Lett. 1982, 23, 5299. (d) Nugent, W. A.; McKinney, R. J.; Harlow, R. L. Organometallics 1984, 3. 1315.
6. Vieira, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865. (b) Black, K. A.; Vogel, P. Helv. Chim. Acta 1984, 67, 1612. (c) Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771. (d) Saf, R.; Faber, K.: Penn. G.: Grienel. H. Tetrahedron 1988, 44. 389.
7. Boone, J. R.; Ashby, E. C. Top. Stereochem. 1979, 11, 53. (b) Ashby, E. C.; Laemmle, J. T. Chem. Rev. 1975, 75, 521.
8. For other additions to the carbonyl group of oxabicyclic ketones, see: (a) Additions of complex metal hydrides to 7-oxabicyclo[2.2.1]hep-tan-one, Moursonides, J.; Wege, D. Aust. J. Chem. 1983, 36, 2473. (b) Hydride reductions of 5,6-exo-epoxy-7-oxabicyclo[2.2.1]heptan-2-one: Le Drian, C.; Vogel, P. Helv. Chim. Acta 1988, 71, 1399. (c) Additions of nitrogen nucleophiles: Arjona, O.; Mallo, A.; Manzano, C.; Plumet, J.; Galbis, J.; Jaime, C. J. Chem. Soc., Perkin Trans. 2 1988, 865. (d) Additions of dichloroketene: Arjona, O.; Fernandez de la Pradilla, R.; Perez, S.; Plumet, J. Tetrahedron 1988, 44, 1235. (e) Addition of me-thyllithium to 3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-2-one: Buchbauer, G.; Holbik, H. Heterocycles 1988, 27, 1217. (f) Addition of the lithium anion of (+)-(S)N, S-dimethyl-S-phenyl sulfoximide to 5-exo,6-exo-(iso-propylidenedioxy)-7-oxabicyclo[2.2.1]heptan-2-one, see ref 4c.
9. For a new approach to predicting the stereochemistry of the addition of nucleophiles to chiral aldehydes and ketones, see: (a) Wu, Y. D.; Houk, K. N. J. Am. Chem. Soc. 1987,109, 908. (b) Wu, Y. D.; Houk, K. N.: Trost, B. M. J. Am. Chem. Soc. 1987. 109. 5560.
10. This behavior is consistent with literature data for norbornenic systems. See, for example: (a) Brown, W. L.; Fallis, A. G. Tetrahedron Lett. 1985, 26, 207. (b) Jung, M. E.; Hatfield, G. L. Tetrahedron Lett. 1983, 24, 2931.
11. See for example: (a) Fleming, I.; Terret, N. K. J. Organomet. Chem. 1984, 264, 99. (b) Kuwajima, I.; Nakamura, E.; Hashimoto, K. Tetrahedron 1983. 39. 975.
12. Trost, B. M.; Florez, J.; Jebaratnam, D. J. J. Am. Chem. Soc. 1987, 109, 613. (b) Trost, B. M.; Florez, J.; Haller, K. J. J. Org. Chem. 1988, 53, 2394.
13. Macdonald, T. L.; Still, W. C. J. Am. Chem. Soc. 1975, 97, 5280. (b) Macdonald, T. L.; Still, W. C. Tetrahedron Lett. 1976, 2659.
14. Lithium organocuprates were generally unreactive toward saturated ketones. For some reports of organocuprate/ketone additions, see: (a) Scott, L. T.; Cotton, W. D. J. Chem. Soc., Chem. Commun. 1973, 320. (b) Goldsmith, D. J.; Sakano, I. Tetrahedron Lett. 1974, 2857. (c) House, H. D.; Chu, C. Y.; Wilkins, J. M.; Umen, M. J. J. Org. Chem. 1975, 40, 1460. (d) Marino, J. P.; Floyd, D. M. Tetrahedron Lett. 1975, 3897.
15. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4371. (b) Lipshutz reports that the addition of 3 equiv of RLi to Cul affords only RoCuLi and free RLi. See: Lipshutz, B. H. Synthesis 1987. 325.
16. It has been recently reported that an ortho-methoxymethyl substituent in a methyl cinnamate system intramolecularly assists the conjugate addition of Me2CuLi. See: Hallnemo, G.; Ullenius, C. Tetrahedron Lett. 1986, 27, 395. For a recent report describing a highly diastereose-lective conjugate addition of organocopper reagents on cinnamates bearing a chiral oxazolidine or imidazolidine ring, see: Alexakis, A.; Sedrani, R.; Mangeney, P.; Normant, J. F. Tetrahedron Lett. 1988, 29, 4411.
17. There are numerous examples in the literature of the “anomalous” behavior of vinyl and phenyl cuprates. See, for example: Marino, J. P.; Jaen, J. C. J. Am. Chem. Soc. 1982, 104, 3165.
18. We thank one of the referees for suggesting this experiment, as well as the use of Ph3Cu2Li and Ph3Cu2Li'2BF3.Et20. (See: Lipshutz, B. H.; Ellsworth, E. L.; Siahaan, T. J. J. Am. Chem. Soc. 1989, 111, 1351). The former species produced a good yield of endo isomer 11, while the latter afforded only recovered starting material. With respect to the generation of Ph3CuLi2 in dimethyl sulfide (negative Gilman test), see: (a) Bertz, S. H.; Dabbagh, G. J. Am. Chem. Soc. 1988, 110, 3668. (b) Bertz, S. H.; Dabbagh, G. Tetrahedron 1989, 2, 45.
19. For a recent review, see: Yamamoto, Y. Angew. Chem., Int. Ed. EngI. 1986, 25, 947.
20. For a detailed study on magnesium methylcuprates, see: Ashby, E. C.; Goel, A. B. J. Org. Chem. 1983, 48, 2125.
21. See for example: Marino, J. P.; Fernandez de la Pradilla, R.; Laborde, E. J. Ore. Chem. 1987, 52, 4898.
22. Jackman, L. M.; Sternhell, S. Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry; Pergamon Press: Oxford. 1969: P 84.
23. Arjona, O.; Fernandez de la Pradilla, R.; Perez, R. A.; Plumet, J.; Viso, A. Tetrahedron Lett. 1987, 28, 5549.
24. This trend is observed for related norbornenic systems. See, for example: Schneider, H. J.; Weigand, E. F.; Becker, N. J. Org. Chem. 1988. 53. 3361.
25. For a report describing the alkylation and oligomerization of the lithium enolate of 2-norbomenone, see: Horner, J. H.; Vera, M.; Grutzner, J. B. J. Org. Chem. 1986, 51, 4212. See also: Turecek, F.; Brabec, L.; Korvola, J. J. Am. Chem. Soc. 1988, 110, 7984.
26. Maruoka, K.; Itoh, T.; Sakurai, M.; Nonoshita, K.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 3588.
27. For a report describing the unexpectedly high trans diastereofa-cial selectivity encountered for cuprate additions to 5-methoxy-2-cyclo-pentenone, see: Smith, A. B. III; Dunlap, N. K.; Sulikowski, G. A. Tetrahedron Lett. 1988, 29, 439. In this contribution, the observed selectivity is accounted for in terms of a novel stereoelectronic effect.
28. Watson, S. C.; Eastham, J. E. J. Organomet. Chem. 1967, 9, 165.
29. Freeman, P. K.; Balls, D. M.; Brown, D. J. J. Org. Chem. 1968, 33, 2211.