One-pot approach to the conversion of alcohols into α-Iodoα, β-unsaturated Esters

Synthetic Communications

Volumn 40, Issue 23, 2010, Pages 3447-3451

  Karama, Usama ^a  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

Iodo , unsaturated esters; iodoylides; one pot synthesis; oxidation

Indexed keywords

ALCOHOL DERIVATIVE; ALPHA IODO ALPHA,BETA UNSATURATED ESTER; ESTER DERIVATIVE; ETHYL 2 IODO 3 PHENYLPROPENOATE; ETHYL 2 IODO 5 PHENYLPENT 2 EN 4 YNOATE; ETHYL 2 IODO 5 PHENYLPENTA 2,4 DIENOATE; ETHYL 2 IODO 5,9 DIMETHYLDECA 2,8 DIENOATE; ETHYL 2 IODOHEPT 2 EN 4 YNOATE; ETHYL 2 IODOHEPTA 2,4 DIENOATE; ETHYL 2 IODONON 2 ENOATE; ETHYL 3 (FURAN 2 YL) 2 IODO 3 PROPENOATE; MANGANESE DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; IODINATION; ONE POT SYNTHESIS; OXIDATION; WITTIG REACTION;

EID: 77952873180     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903434570     Document Type: Article

References (14)

1. Nicolaou, K. C.; Haerter, M. W.; Gunzner, J. L.; Nadine, A. The Wittig and related reactions in natural product synthesis. Liebigs Ann.=Recueil. 1997, 1283-1301.
2. Wei, X.; Taylor, R. J. K. In situ manganese dioxide alcohol oxidation-Wittig reactions: Preparation of bifunctional dienyl building blocks. J. Org. Chem. 2000, 65 (2), 616-620.
3. Zhang, X.; Zhong, P.; Chen, F. A facile one-pot synthesis of a-iodo-a,b-unsaturated esters. Synth. Commun. 2004, 34 (9), 1729-1736.
4. Denney, D. B.; Ross, S. T. The preparation and reaction of some halophosphoranes. J. Org. Chem. 1962, 27 (3), 998-1000.
5. Speziale, A. J.; Ratts, K. W. Reaction of phosphorus compounds v. resonance-stabilized a-halomethylenephosphoranes. J. Org. Chem. 1963, 28 (2), 465-469.
6. Kayser, M. M.; Zhu, J.; Hooper, D. L. Stabilized haloylides: synthesis and reactivity. Can. J. Chem. 1997, 75, 1315-1321.
7. Zhang, X.; Qing, F. L.; Yihua, Y. Synthesis of 2,3-dideoxy-2- trifluoromethylnucleosides from a-trifluoromethyl-a,b-unsaturated ester. J. Org. Chem. 2000, 65, 7075-7082.
8. Zhang, X. G.; Qing, F. L.; Yang, Y.; Yu, J.; Fu, X. K. A new route to a-trifluoromethyl-a,b-unsaturated esters. Tetrahedron Lett. 2000, 41 (16), 2935-2956.
9. Tago, K.; Kogen, H. Bis(2,2,2-trifluoroethyl)bromophosphonoacetate, a novel HWE reagent for the preparation of (E)-a-bromoacrylates: A general and stereoselective method for the synthesis of trisubstituted alkenes-a,b- unsaturated esters. Org. Lett. 2000, 13, 1975-1978.
10. Qing, F. L.; Zhang, X. A one-pot synthesis of (E)-a-trifluoromethyl-a,b- unsaturated esters. Tetrahedron Lett. 2001, 42, 5929-5931.
11. Frison, N.; Folleas, B.; Brayer, J. L. New method for preparing unsaturated fatty hydroxyl acids. PCT Int. Appl. WO Patent 084062 A1, 2008.
12. Blackburn, L.; Wei, X.; Taylor, R. J. K. Manganese dioxide can oxidize unactivated alcohols under in situ oxidation-Wittig conditions. Chem. Commun. 1999, 1337-1338.
13. Deng, G. S.; Liu, C. Y. One-pot approach to the conversion of alcohols into a-halo-a,b-unsaturated esters. Chin. Chem. Lett. 2006, 17329-17332.
14. Karama, U. A one-pot synthesis of (E)-a-chloro-a,b-unsaturated esters. J. Chem. Res. 2009, 7, 405-406.