Methylenation of carbonyl compounds by means of Nysted reagent

Synlett

Volumn , Issue 3, 1998, Pages 313-315

  Matsubara, Seijiro ^a   Sugihara, Masakazu ^a   Utimoto, Kiitiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001261158     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-36073     Document Type: Article

References (20)

1. Maercker, A. Org. React., 1965, 14, 270;
2. Maryanoff, B. E.; Reits, A. B. Chem. Rev., 1989, 89, 863.
3. Schrock, R. R.; Depue, R. T.; Feldman, J.; Yap, K. B.; Yang, D. C.; Davis, W. M.; Park, L.; Dimare, M.; Schofield, M.; Anhaus, J.; Walborsky, E.; Evitt, E.; Kruger, C.; Betz, P. Organometallics, 1990, 9, 2262.
4. Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc., 1978, 700, 3611;
5. Clawson, L.; Buchwald, S. L.; Grubbs, R. H. Tetrahedron Lett., 1984, 25, 5733.
6. Petasis, N. A.; Browej, E. I. J. Am. Chem. Soc., 1990, 112, 6392;
7. Petasis, N. A.; Browej, E. I. J. Org. Chem., 1992, 57, 1327;
8. Petasis, N. A.; Staszewski, J. P.; Fu, D. K. Tetrahedron Lett., 1995, 36, 3619.
9. Marek, I.; Normant, J. F. Chem. Rev., 1996, 96, 3241.
10. Takai, K.; Hotta, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett., 1978, 2417;
11. Hibino, J.-I.; Okazoe, T.; Takai, K.; Nozaki, H. Tetrahedron Lett., ibid., 1986, 26, 5579 and 5581;
12. Lombardo, Org. Synth. 1987, 65, 81.
13. Okazoe, T.; Takai, K.; Oshima, K.; Utimoto, K. J. Org. Chem., 1987, 52, 4410;
14. Takai, K.; Kataoka, Y.; Miyai, J.; Okazoe, T.; Oshima, K.; Utimoto, K. Org. Synth. 1996, 75, 73.
15. The Nysted reagent (L. N. Nysted, US Patent 3 865 848, 1975; Chem. Abstr. 1975, 83, 10406q) is commercially available from Aldrich Co. Preparation of the Nysted reagent uses zinc-lead couple or zinc activated with hydrochloric acid.
16. Tochtermann, W.; Bruhn, S.; Meints, M.; Wolff, C.; Peters, E-M., Peters, K.; von Schnering, H. G. Tetrahedron, 1995, 51, 1623 ;
17. Gleiter, R.; Herb, T.; Hofmann, J. Synlett, 1996, 987.
18. The data also indicated that commercial Nysted reagent keeps original concentration.
19. Purity was determined by glc using chiral column; Chrompack, CP-Chiralsil-DexCB, 25 m × 0.25 mm.
20. Narula, S. P.; Sharma, H. K. Inorg. Syn., 1985, 24, 181.