Reaction of methylcerium reagent with tertiary amides: Synthesis of saturated and unsaturated ketones from tertiary amides

Tetrahedron Letters

Volumn 39, Issue 27, 1998, Pages 4793-4796

  Kurosu, Michio ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; AMIDE; KETONE; METHYLCERIUM; MORPHOLINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032474882     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00959-9     Document Type: Article

References (16)

1. 1. For synthetic work from this laboratory, see: (a) Grinsteiner, T. J.; Kishi, Y. Tetrahedron Lett. 1994, 35 8333.
2. (b) Grinsteiner, T. J.; Kishi, Y. Tetrahedron Lett. 1994, 35, 8377.
3. 2. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
4. 3. (a) Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233.
5. (b) Imamoto, T.; Sugiura, Y. J. Organomet. Chem. 1985, 285, C21.
6. (c) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904.
7. (d) Imamoto, T. Pure & Appl. Chem. 1990, 62, 747.
8. 4. For a review of the use of organolanthanides in organic synthesis, see: Molander, G. A. Chem. Rev. 1992, 92, 29.
9. 5. For an attempt to characterize the composition of organocerium reagents, see: Denmark, S. E.; Edwards, J. P.; Nicaise, O. J. Org. Chem. 1993, 58, 569.
10. 6. For ultrasound-assisted preparation of organocerium reagent, see: Greeves, N.; Lyford, L. Tetrahedron Lett. 1992, 33, 4759.
11. 2O, see: Dimitrov, V.; Kostova, K.; Genov, M. Tetrahedron Lett. 1996, 37, 6787.
12. 2" solution to yield the tertiary alcohol quantitatively.
13. 9. For the reaction of alkyllanthanum triflate with hindered tertiary amides, see: Collins, S.; Hong, Y.; Hoover, G. J.; Veit, J. R. J. Org. Chem. 1990, 55, 3565.
14. 10. This substrate was prepared from estrone by adopting the method reported by Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1985, 26, 1109.
15. 11. Kurosu, M.; Marcin, L. R.; Grinsteiner, T. J.; Kishi, Y., submitted for publication.
16. 12. The reaction of other THF-soluble alkyl and alkenyl cerium species, including the reagent prepared from butyllithium and 1-ethoxyvinyllithium, has been studied thus far: Kurosu, M.; Marcin, L. R.; Kishi, Y., unpublished results.