Diethylaminotrimethylsilane mediated aldol condensation of naked aldehydes

Tetrahedron Letters

Volumn 40, Issue 36, 1999, Pages 6627-6630

  Hagiwara, Hisahiro ^a   Ono, Hiroki ^a   Komatsubara, Nao ^a   Hoshi, Takashi ^a   Suzuki, Toshio ^a   Ando, Masayoshi ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

Aldehydes; Aldol reactions; Enals

Indexed keywords

ALDEHYDE; SILANE DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION;

EID: 0033520240     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01326-X     Document Type: Article

References (20)

1. (a) Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc., 1963, 85, 207-222.
2. (b) Brown, M. J. Org. Chem., 1968, 33, 162-165.
3. Duhamel, P.; Hennequin, L.; Poirier, J. M.; Tavel, G.; Vottero, C. Tetrahedron, 1986, 42, 4777-4786.
4. Nakajima, T.; Maruyama, Y.; Shimizu, Y. Abstracts of Papers of 65th Annual Meeting of Chemical Society of Japan, 1993, Tokyo, (Abstract II, p 335).
5. Haussermann, M. Helv. Chim. Acta, 1951, 34, 1482-1491.
6. Casnati, G.; Pochini, A.; Salerno, G.; Ungaro, R. Tetrahedron Lett., 1974, 959-962.
7. Offenhauer, R. D.; Nelsen, S. F. J. Org. Chem., 1968, 33, 774-777.
8. Cossu-Jouve, M.; Savon, M.-C.; Uccjiani, E. Bull. Soc. Chim. Fr., 1973, 2429.
9. Shono, T.; Kashimura, S.; Ishizaki, K. Electrochim. Acta, 1984, 29, 603.
10. (a) Alder, K.; Haydn, J.; Heimbach, K.; Neufang, K. Justus Liebigs Ann. Chem., 1954, 586, 110.
11. (b) Payne, G. B.; Williams, P. H. J. Org. Chem., 1961, 26, 651-659.
12. Keskin, H.; Miller, R. E.; Nord, F. F. J. Org. Chem., 1951, 16, 199-206.
13. Lipp, M.; Dallacker, F. Chem. Ber., 1957, 90, 1730-1734.
14. Ishikawa, T.; Uedo, E.; Okada, S.; Saito, S. Synlett, 1999, 450-452.
15. Middleton, W. J.; Bingham, E. M. in Org. Synth., Ed. Noland, W. E. John Wiley & Sons, New York, 1988, collective volume 6, p. 440-441.
16. A part of this work was presented in 74th Annual Meeting of Chemical Society of Japan, March 1998, Kyoto (Abstract II, p 1448).
17. Hagiwara, H.; Kato, M. Tetrahedron Lett., 1996, 37, 5139-5140.
18. Hagiwara, H.; Komatsubara, N.; Hoshi, T.; Suzuki, T.; Ando, M. Tetrahedron Lett., 1999, 40, 1523-1526.
19. The relative stereochemistry of quaternary carbon can not be determined at this stage.
20. 2NTMS (95 μl, 0.5 mmol) was heated at 50 °C for 16 hr under nitrogen atmosphere. The resulting mixture was evacuated in vacuo and the residue was separated by medium pressure liquid chromatography (eluent: n-haxane:ethyl acetate = 5:1) to give enal 1a (68 mg, 51%).