Allylation of cyclohexanones in aqueous media and influence of facial amphiphilic fructopyranosides

Tetrahedron Letters

Volumn 51, Issue 38, 2010, Pages 4934-4936

  Bellomo, Ana ^a,b   Daniellou, Richard ^a,b   Plusquellec, Daniel ^a,b  

^a UNIV RENNES   (France)

^b UNIVERSITÉ EUROPÉENNE DE BRETAGNE   (France)

Author keywords

Allylation; Facial amphiphilic sugars; Water

Indexed keywords

CARBOHYDRATE; CYCLOHEXANONE; INDIUM; PYRANOSIDE; WATER;

ALLYLATION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY;

EID: 78549267121     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.028     Document Type: Article

References (21)

1. Li, C.-J. Tetrahedron 1996, 52, 5643-5668.
2. Li, C.-J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017-7020.
3. Lindstrom, U. M. Chem. Rev. 2002, 102, 2751-2772.
4. Nair, V.; Ros, S.; Jayan, C. N.; Pillai, B. S. Tetrahedron 2004, 60, 1959-1982.
5. Paquette, L. A. Synthesis 2003, 2003, 0765-0774.
6. Li, C.-J.; Chen, D.-L.; Lu, Y.-Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216-4217.
7. Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500-5507.
8. Ashby, E. C.; Laemmle, J. T. Chem. Rev. 1975, 75, 521-546.
9. Maruoka, K.; Itoh, T.; Sakurai, M.; Nonoshita, K.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 3588-3597.
10. Denis, C.; Laignel, B.; Plusquellec, D.; Le Marouille, J.-Y.; Botrel, A. Tetrahedron Lett. 1996, 37, 53-56.
11. Denis, C.; Misbahi, K.; Kerbal, A.; Ferrieres, V.; Plusquellec, D. Chem. Commun. 2001, 2460-2461.
12. Lubineau, A.; Auge, J.; Scherrmann, M.-C. In Organic Chemistry in Water; Wiley- VCH, 2004.
13. Koszinowski, K. J. Am. Chem. Soc. 2010, 132, 6032-6040.
14. A mixture of allyl bromide (152.9 mg, 1.26 mmol), indium powder (150.8 mg, 1.31 mmol), cyclohexanone 1 (0.82 mmol), and water (6.0 mL) or 1 M aqueous sugar solution (1.0 mL) was stirred vigorously at room temperature. The reaction mixture was kept on being stirred and gradually became milky white.
15. Once ketone consumption was complete as demonstrated by TLC analysis, the reaction was quenched with 10% HCl, and the reaction mixture was extracted with ether (3 × 10 mL).
16. 4 and concentrated under vacuum. After separation by chromatography on silica gel, compounds 2a-g were characterized by NMR spectroscopy.
17. Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917-1930.
18. Reetz, M. T.; Haning, H. J. Organomet. Chem. 1997, 541, 117-120.
19. Haraguchi, Y.; Yagi, A.; Koda, A.; Inagaki, N.; Noda, K.; Nishioka, I. J. Med. Chem. 1982, 25, 1495-1499.
20. Raaijmakers, H. W. C.; Arnouts, E. G.; Zwanenburg, B.; Chittenden, G. J. F. Carbohydr. Res. 1994, 257, 293-297.
21. Ferrières, V.; Benvegnu, T.; Lefeuvre, M.; Plusquellec, D.; Mackenzie, G.; Watson, M. J.; Haley, J. A.; Goodby, J. W.; Pindak, R.; Durbin, M. K. J. Chem. Soc., Perkin Trans. 2 1999, 951-959.