The effects of amine and acid catalysts on efficient chelation-assisted hydroacylation of alkene with aliphatic aldehyde

Tetrahedron Letters

Volumn 50, Issue 26, 2009, Pages 3338-3340

  Jo, Eun Ae ^a   Jun, Chul Ho ^a  

^a Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

4 TRIFLUOROMETHYLBENZOIC ACID; ALDEHYDE; ALKENE; BENZOIC ACID DERIVATIVE; BETA AMINOALDIMINE; ETICYCLIDINE; HEXYLAMINE; IMINE; PICOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ALDOL REACTION; ARTICLE; CATALYST; CHELATION; CONJUGATE; CYCLOADDITION; FRAGMENTATION REACTION;

EID: 65549097756     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.091     Document Type: Article

References (21)

1. Stemmler R.T., and Bolm C. Adv. Synth. Catal. 349 (2007) 1185-1198
2. Willis M.C., McNally S.J., and Beswick P.J. Angew. Chem., Int. Ed. 43 (2004) 340-343
3. Moxham G.L., Randell-Sly H.E., Brayshaw S.K., Woodward R.L., Weller A.S., and Willis M.C. Angew. Chem., Int. Ed. 45 (2006) 7618-7622
4. Roy A.H., Lenges C.P., and Brookhart M. J. Am. Chem. Soc. 129 (2007) 2082-2093
5. Imai M., Tanaka M., Nagumo S., Kawahara N., and Suemune H. J. Org. Chem. 72 (2007) 2543-2546
6. Willis M.C., Randell-Sly H.E., Woodward R.L., and Currie G.S. Org. Lett. 7 (2005) 2249-2251
7. Tanaka K., Shibata Y., Suda T., Hagiwara Y., and Hirano M. Org. Lett. 9 (2007) 1215-1218
8. Jun C.-H., Jo E.-A., and Park J.-W. Eur. J. Org. Chem. (2007) 1869-1881
9. Jun C.-H., Lee H., and Hong J.-B. J. Org. Chem. 62 (1997) 1200-1201
10. Jun C.-H., Lee D.-Y., Lee H., and Hong J.-B. Angew. Chem., Int. Ed. 39 (2000) 3070-3072
11. Jun C.-H., Huh C.-W., and Na S.-J. Angew. Chem., Int. Ed. 37 (1998) 145-147
12. Lee D.-Y., Kim I.-J., and Jun C.-H. Angew. Chem., Int. Ed. 41 (2002) 3031-3033
13. Jun C.-H., Lee H., Moon C.W., and Hong H.-S. J. Am. Chem. Soc. 123 (2001) 8600-8601
14. Lee D.-Y., Hong B.-S., Cho E.-G., Lee H., and Jun C.-H. J. Am. Chem. Soc. 125 (2003) 6372-6373
15. Synthesis of 2-benzyl-5-phenyl-pent-2-enal (7a): Three millilitres of an aqueous NaOH solution (10%) were slowly added to hydrocinnamaldehyde (1a, 0.05 mol, 6.7 g) diluted in 50 ml of tetrahydrofuran (THF). Then the reaction mixture was stirred at room temperature for 12 h and neutralized with an aqueous solution of HCl (10%), and ether was added. The organic phase was dried on magnesium sulfate before filtration and purified via column chromatography (n-hexane ethyl acetate = 10:1) to give 3.9 g of 7a.
16. Jun C.-H., and Lee H. J. Am. Chem. Soc. 121 (1999) 880-881
17. Jun C.-H., Lee H., Park J.B., and Lee D.-Y. Org. Lett. 1 (1999) 2161-2164
18. 3RhCl (3), 6.5 mg (0.06 mmol) of 2-amino-3-picoline (4), 2.4 mg (0.02 mmol) of p-trifluoromethylbenzoic acid (5b), 7.9 mg (0.08 mmol) of cyclohexylamine (8) and 100 mg of toluene. The reaction mixture was sealed and stirred for 1 h in an oil bath that was preheated at 110 °C. After cooling to room temperature, the organic layer was analyzed on a GCD system to be a compound mixture of 6,6-dimethyl-1-phenylheptan-3-one (6a) and 2-benzyl-5-phenyl-2-pentenal (7a) in 61% and 39% ratio.
19. It can be also speculated that a small amount of aldehyde may be directly transformed to hydroacylation product without generating aldol condensation intermediate.
20. Jun C.-H., and Hong J.-B. Org. Lett. 1 (1999) 887-889
21. 30O: C, 79.58; H, 13.36; Found: C, 79.56; H, 13.24.