Chlorodimethylaluminum-promoted nucleophilic addition of lithium pentamethylcyclopentadienide to aliphatic aldehydes and DDQ-mediated carbon-carbon bond cleavage of the adducts providing the parent aldehydes

Tetrahedron Letters

Volumn 47, Issue 2, 2006, Pages 163-166

  Uemura, Minoru ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Carbon carbon bond cleavage; Chlorodimethylaluminum; Nucleophilic addition; Pentamethylcyclopentadiene

Indexed keywords

2,3 DICHLORO 5,6 DICYANOBENZOQUINONE; ALDEHYDE; ALKENE DERIVATIVE; ALUMINUM DERIVATIVE; BENZOQUINONE DERIVATIVE; CARBON; CHLORODIMETHYLALUMINUM; LITHIUM DERIVATIVE; LITHIUM PENTAMETHYLCYCLOPENTADIENIDE; METHANOL DERIVATIVE; PENTAMETHYLCYCLOPENTADIENE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL BOND; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 28644451348     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.159     Document Type: Article

References (24)

1. K. Yagi, H. Yorimitsu, and K. Oshima Tetrahedron Lett. 46 2005 4831 4833
2. - to carbonyl compounds: L. de Vries J. Org. Chem. 25 1960 1838
3. F.X. Kohl, and P. Jutzi Chem. Ber. 120 1987 1539 1543
4. H.-A. Brune, P. Lach, and G. Schmidtberg Chem. Ber. 118 1985 2671 2680
5. H.-A. Brune, P. Lach, and G. Schmidtberg Chem. Ber. 118 1985 2681 2691
6. H. Otto, and H. Werner Chem. Ber. 120 1987 97 104
7. P. Jutzi, K.-H. Schwartzen, A. Mix, H.-G. Stammler, and B. Neumann Chem. Ber. 126 1993 415 420
8. R.F. Childs, and M. Zeya J. Am. Chem. Soc. 96 1974 6418 6424
9. Recent examples of metal-mediated carbon-carbon bond cleavage reactions of tertiary alcohols: Y. Terao, H. Wakui, T. Satoh, M. Miura, and M. Nomura J. Am. Chem. Soc. 123 2001 10407 10408
10. T. Nishimura, K. Ohe, and S. Uemura J. Org. Chem. 66 2001 1455 1465
11. S.-B. Park, and J.K. Cha Org. Lett. 2 2000 147 149
12. H. Okumoto, T. Jinnai, H. Shimizu, Y. Harada, H. Mishima, and A. Suzuki Synlett 2000 629 630
13. T. Kondo, K. Kodoi, E. Nishinaga, T. Okada, Y. Morisaki, Y. Watanabe, and T. Mitsudo J. Am. Chem. Soc. 120 1998 5587 5588
14. P. Jones, and P. Knochel J. Org. Chem. 64 1999 186 195
15. C.-K. Choi, I. Tomita, and T. Endo Chem. Lett. 1999 1253 1254
16. Z. Hou, T. Koizumi, A. Fujita, H. Yamazaki, and Y. Wakatsuki J. Am. Chem. Soc. 123 2001 5812 5813
17. T. Ooi, T. Miura, and K. Maruoka J. Am. Chem. Soc. 120 1998 10790 10791
18. T. Ooi, T. Miura, K. Ohmatsu, A. Saito, and K. Maruoka Org. Biomol. Chem. 2 2004 3312 3319
19. S. Hayashi, K. Hirano, H. Yorimitsu, and K. Oshima Org. Lett. 7 2005 3577 3579
20. E.A. Braude, L.M. Jackman, and R.P. Linstead J. Chem. Soc. 1954 3548 3563
21. E.S. Lewis, J.M. Perry, and R.H. Grinstein J. Am. Chem. Soc. 92 1970 899 905
22. P.J. van der Jagt, H.K. de Haan, and B. van Zanten Tetrahedron 27 1971 3207 3214
23. DDQ can abstract the hydride at the 3-methyl group of the Cp* group.
24. M. Abe, and A. Oku Tetrahedron Lett. 35 1994 3551 3554