Diastereoselection in the conjugate additions of organocopper reagents to N-enoyloxazolidinones

Tetrahedron Letters

Volumn 39, Issue 47, 1998, Pages 8593-8596

  Williams, David R ^a   Kissel, William S ^a   Li, Jie Jack ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CONJUGATION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032547974     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01966-2     Document Type: Article

References (19)

1. 1. For a review: Rossiter, B.E.; Swingle, N.M. Chem. Rev. 1992, 92, 771.
2. 2. a) Oppolzer, W.; Löher, H.J. Helv. Chim. Acta, 1981, 64, 2808.
3. b) Oppolzer, W.; Stevenson, T. Tetrahedron Lett. 1986, 27, 1139.
4. 3. Tomioka, K.; Suenaga, T.; Koga, K. Tetrahedron Lett. 1986, 27, 369.
5. 4. a) For cuprate additions: Pourcelot, G.; Aubouet, J.; Caspar, A.; Cresson, P. J. Organomet. Chem. 1987, 328, C43. Melnyk, O.; Stephan, E.; Pourcelot, G.; Cresson, P. Tetrahdron, 1992, 48, 841.
6. 4. a) For cuprate additions: Pourcelot, G.; Aubouet, J.; Caspar, A.; Cresson, P. J. Organomet. Chem. 1987, 328, C43. Melnyk, O.; Stephan, E.; Pourcelot, G.; Cresson, P. Tetrahdron, 1992, 48, 841.
7. b) For mono-organocopper additions: Van Heerden, P.S.; Bezuidenhoudt, B.C.B.; Ferreira, D. Tetrahedron Lett. 1997, 38, 1821.
8. 5. a) For aryl cuprate additions: Nicolàs, E.; Russell, K.C.; Hruby, V.J. J. Org. Chem. 1993, 58 766.
9. b) For CuBr-catalyzed aryl Grignard additions: Li, G.; Jarosinski, M.A.; Hruby, V.J. Tetrahedron Lett. 1993, 34, 2561. Liao, S.; Han, Y.; Qui, W.; Bruck, M.; Hruby, V.J. Tetrahedron Lett. 1996, 37, 7917.
10. b) For CuBr-catalyzed aryl Grignard additions: Li, G.; Jarosinski, M.A.; Hruby, V.J. Tetrahedron Lett. 1993, 34, 2561. Liao, S.; Han, Y.; Qui, W.; Bruck, M.; Hruby, V.J. Tetrahedron Lett. 1996, 37, 7917.
11. 6. Williams, D.R.; Li, J. Tetrahedron Lett. 1994, 35, 5113.
12. 7. These results have been discussed in our presentation of the total synthesis of amphidinolide J. See: Williams, D.R.; Kissel, W.S. American Chemical Society 214th National Meeting; Las Vegas, NV; Sept. 10, 1997; Abstr. 279. Also: Rzasa, R.M.; Shea, H.A.; Romo, D. J. Am. Chem. Soc. 1998, 120, 591.
13. 7. These results have been discussed in our presentation of the total synthesis of amphidinolide J. See: Williams, D.R.; Kissel, W.S. American Chemical Society 214th National Meeting; Las Vegas, NV; Sept. 10, 1997; Abstr. 279. Also: Rzasa, R.M.; Shea, H.A.; Romo, D. J. Am. Chem. Soc. 1998, 120, 591.
14. 8. Yamamoto, Y. Angew. Chem. Int. Ed. Engl. 1986, 25, 947.
15. 1H NMR δ 7.65 (d, J = 8.0 Hz, 4H), 7.43-7.24 (m, 11H), 5.40 (dd, J = 8.6, 3.7 Hz, 1H), 4.78 (s, 1H), 4.66 (s, 1H), 4.66 (t, J = 8.8 Hz, 1H), 4.26 (dd, J = 8.9, 3.7 Hz, 1H), 3.70 (m, 2H), 3.12 (dd, J = 16.3, 5.5 Hz, 1H), 2.82 (dd, J = 16.0, 9.0 Hz, 1H), 2.62 (m, 1H), 2.25 (t, J = 7.0 Hz, 2H), 1.03 (s, 9H), 0.97 (d, J = 7.0 Hz, 3H).
16. 2AlCl (2 equivs) was premixed with oxazolidinone 5 or 6, addition of vinylcopper occurred at -78 °C in 4 hours. Recently a related study of TMSCl promoted conjugate addition of vinyl Grignard has appeared. See: Han, Y.; Hruby, V.J. Tetrahedron Lett. 1997, 38, 7317.
17. 11. Castellino, S.; Dwight, W.J. J. Am. Chem, Soc. 1993, 115, 2986.
18. 12. Bergdahl, M.; Iliefski, T.; Nilsson, M.; Olsson, T. Tetrahedron Lett. 1995, 36, 3227.
19. 4. Amoroso, R.; Cardillo, G.; Sabatino, P.; Tomasini, C.; Trerè, A. J. Org. Chem. 1993, 58, 5615.