Methylenation of esters with bis(iodozincio)methane-TiCl2-TMEDA system

Chemistry Letters

Volumn , Issue 8, 1999, Pages 825-826

  Matsubara, Seijiro ^a   Ukai, Katsumi ^a   Mizuno, Tsuyoshi ^a   Utimoto, Kiitiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033245581     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.825     Document Type: Article

References (19)

1. A. Maercker, Org. React., 14, 270 (1965); B.E. Maryanoff and A.B. Reits,Chem. Rev., 89, 863 (1989).
2. A. Maercker, Org. React., 14, 270 (1965); B.E. Maryanoff and A.B. Reits,Chem. Rev., 89, 863 (1989).
3. a) I. Marek and J.-F. Normant, Chem. Rev., 96, 3241 (1996).
4. b) L. Lombardo, Org. Synth., 65 81 (1987).
5. c) K. Takai, Y. Kataoka, J. Miyai, T. Okazoe, K. Oshima, and K. Utimoto, Org. Synth., 73, 73 (1996).
6. d) J. Hibino, T. Okazoe, K. Takai, and H. Nozaki, Tetrahedron Lett., 26, 5579 and 5581 (1996).
7. e) By Nysted reagent: S. Matsubara, M. Sugihara, K. Utimoto, Synlett, 1998, 313; L. N. Nysted, US Patent 3 865 848 (1975); Chem. Abstr., 83, 10406q (1975).
8. e) By Nysted reagent: S. Matsubara, M. Sugihara, K. Utimoto, Synlett, 1998, 313; L. N. Nysted, US Patent 3 865 848 (1975); Chem. Abstr., 83, 10406q (1975).
9. e) By Nysted reagent: S. Matsubara, M. Sugihara, K. Utimoto, Synlett, 1998, 313; L. N. Nysted, US Patent 3 865 848 (1975); Chem. Abstr., 83, 10406q (1975).
10. R.R. Schrock, R.T. Depue, J. Feldman, K.B. Yap, D.C. Yang, W.M. Davis, L. Park, M. Dimare, M. Schofield, J. Anhaus, E. Walborsky, E. Evitt, C. Kruger, and P. Betz, Organometallics, 9, 2262 (1990).
11. F.N. Tebbe, G.W. Parsnall, and G.S. Reddy, J. Am. Chem. Soc., 100, 3611 (1978); L. Clawson, S.L. Buchwald, and R.H. Grubbs, Tetrahedron Lett., 25, 5733 (1984); N.A. Petasis and E.I. Browej, J. Am. Chem. Soc., 112, 6392 (1990).
12. F.N. Tebbe, G.W. Parsnall, and G.S. Reddy, J. Am. Chem. Soc., 100, 3611 (1978); L. Clawson, S.L. Buchwald, and R.H. Grubbs, Tetrahedron Lett., 25, 5733 (1984); N.A. Petasis and E.I. Browej, J. Am. Chem. Soc., 112, 6392 (1990).
13. F.N. Tebbe, G.W. Parsnall, and G.S. Reddy, J. Am. Chem. Soc., 100, 3611 (1978); L. Clawson, S.L. Buchwald, and R.H. Grubbs, Tetrahedron Lett., 25, 5733 (1984); N.A. Petasis and E.I. Browej, J. Am. Chem. Soc., 112, 6392 (1990).
14. a) T. Okazoe, K. Takai, K. Oshima, and K. Utimoto, J. Org. Chem., 52, 4410 (1987).
15. b) T. Takeda, R. Sasaki, and T. Fujiwara, J. Org. Chrem., 63, 7286 (1998).
16. S. Matsubara, T. Mizuno, Y. Otake, M. Kobara, K. Utimoto, K. Takai, Synlett, 1998, 1369.
17. S.P. Narula and H.K. Sharma, Inorg. Syn., 24, 181 (1985).
18. 2 with 1 (6.0 mmol), and TMEDA (8.0 mmol) gave 4a in 15% yield. See also Ref 5a.
19. J.F. Remenar, B.L. Lucht, D. Kruglyak, F.E. Romesberg, J.H. Gilchirst, and D.B. Collum, J. Org. Chem., 62, 5748 (1997).