Asymmetric synthesis of functionalised cyclopentenones via organocatalysed rearrangement and enzymatic resolution of pyranones

Tetrahedron Letters

Volumn 50, Issue 26, 2009, Pages 3706-3708

  Nunes, João P M ^a   Afonso, Carlos A M ^a   Caddick, Stephen ^b  

^a Centro de Quimica Fisica Molecular   (Portugal)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Chiral cyclopentenone; Enzymatic resolution; Isomerisation; Organocatalysis; Pyranone; Rearrangement

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; CYCLOPENTENONE DERIVATIVE; PYRAN DERIVATIVE; PYRANONE; TERT BUTYL ALCOHOL; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; ENANTIOMER; GAS CHROMATOGRAPHY; ONE POT SYNTHESIS; REACTION TIME; SOLVENT EFFECT; STEREOCHEMISTRY; SUBSTITUTION REACTION; TEMPERATURE;

EID: 65549146939     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.212     Document Type: Article

References (11)

1. Caddick S., Khan S., Frost L.M., Smith N.J., Cheung S., and Pairaudeau G. Tetrahedron 56 (2000) 8953-8958
2. Caddick S., and Khan S. Chem. Commun. (1995) 1971-1972
3. Arjona O., Gómez A.M., López J.C., and Plumet J. Chem. Rev. 107 (2007) 1919-2036
4. Caddick S., Cheung S., Doyle V.E., Frost L.M., Soscia M.G., Delisser V.M., Williams M.R.V., Etheridge Z.C., Khan S., Pairaudeau G., and Vile S. Tetrahedron 57 (2001) 6295-6303
5. Klomklao T., Pyne S.G., Baramee A., Skelton B.W., and White A.H. Tetrahedron: Asymmetry 14 (2003) 3885-3889
6. Pohmakotr M., Kambutong S., Tuchinda P., and Kuhakarn C. Tetrahedron 64 (2008) 6315-6323
7. Li S.W., and Batey R.A. Chem. Commun. (2007) 3759-3761
8. Caddick S., and Etheridge Z.C. Tetrahedron: Asymmetry 15 (2004) 503-507
9. Vongvilai P., Larsson R., and Ramström O. Adv. Synth. Catal. 350 (2008) 448-452
10. 1H NMR) as a yellow low-melting point solid (170 mg, 85%).
11. 2 (20 mL). The mother liquor was concentrated under reduced pressure to yield a brown oil which was purified by chromatography on silica gel with n-hexane/ethyl acetate (3:1 v/v) to afford (-)-4 as a white low-melting point solid (68 mg, 55%, ee 80%) and (+)-2 and 3 (32 mg, 35%, ee of (+)-2 of 11%) in a 91:9 ratio (determined by GLC) as a yellow low melting point solid.