One-pot combination of the wittig olefination with bromination and oxidation reactions

Synthetic Communications

Volumn 43, Issue 6, 2013, Pages 893-898

  Karama, Usama ^a   Mahfouz, Refat ^a   Al Othman, Zeid ^a   Warad, Ismail ^a   Almansour, Abdulrahman ^a  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

Halogenation; olefination; one pot synthesis; oxidation

Indexed keywords

(ETHOXYCARBONYLMETHYLENE)TRIPHENYLPHOSPHORANE; ALCOHOL; ALDEHYDE; EHYL 3 (FURAN 2 YL) 2 BROMO 3 PROPENOATE; ESTER DERIVATIVE; ETHYL 2 BROMO 3 PHENYLPROPENOATE; ETHYL 2 BROMO 5 PHENYLPENT 2 EN 4 YNOATE; ETHYL 2 BROMO 5 PHENYLPENTA 2,4 DIENOATE; ETHYL 2 BROMOHEPT 2 EN 4 YNOATE; ETHYL 2 BROMOHEPTA 2,4 DIENOATE; ETHYL 2 BROMONON 2 ENOATE; ETHYL 2 BROMONON 5,9 DIMETHYLDECA 2,8 DIENOATE; PHOSPHORANE DERIVATIVE; PYRIDINE; SULFURIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; HALOGENATION; ISOMERISM; OLEFINATION; ONE POT SYNTHESIS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; WITTIG REACTION;

EID: 84871843090     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.614712     Document Type: Article

References (18)

1. Maryanoff, B. E.; Reitz, A. B. The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Chem. Rev. 1989, 89, 863-927.
2. Nicolaou, K. C.; Haerter, M. W.; Gunzner, J. L.; Nadin, A. The Wittig and related reactions in natural product synthesis. Liebigs Ann. Recueil 1997, 1283-1301.
3. 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.
4. Bressette, A. R.; Glover, L. C. A convenient one-pot PCC oxidation-Wittig reaction of alcohols. Synlett 2004, 4, 738-740.
5. 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, 616-620.
6. Blackburn, L.; Kanno, H.; Taylor, J. In situ alcohol oxidation-Wittig reactions using N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide: Application to the synthesis of a novel analogue of 5-oxo-eicosatetraenoic acid. Tetrahedron Lett. 2003, 44, 115-118.
7. Crisostomo, F.; Carrillo, R.; Martin, T.; Tellado, F.; Martin, V. A convenient and chemoselective one-pot oxidation=Wittig reaction for the C2-homologation of carbohydratederived glycols. J. Org. Chem. 2005, 70, 10099-10101.
8. Zhanh, X.; Qing, F. L.; Yu, Y. Synthesis of 2,3-dideoxy-2- trifluoromethylnucleosides from a-trifluoromethyl-a,b-unsaturated ester. J. Org. Chem. 2000, 65, 7075-7082.
9. Keiko, T.; Kogen, H. Bis(2,2,2-trifluoroethyl)bromophosphonoacetate, a novel HWE reagent for the preparation of (E)-bromoacrylates: A general and stereoselective method for the synthesis of trisubstituted alkenes. Org. Lett. 2000, 13, 1975-1978.
10. Wipf, P.; Henningen, T. C.; Geib, S. J. Methyl and trifluoromethyl alkene peptide isosters: Synthesis and evaluation of their potential as b-turn promoters and peptide mimetics. J. Org. Chem. 1998, 63, 6088-6089.
11. Johnson, T. R.; Silvenman, R. B. Synthesis of (Z)-and (E)-4-amino-2-(trifluoromethyl)-2-butenoic acid and their inactivation of gamma-aminobutyric acid aminotransferase. Bioorg. Med. Chem. 1999, 7, 1625-1636.
12. Zhang, X.; Zhong, P.; Chen, F. A facile one-pot synthesis of a-iodo-a,b-unsaturated esters. Synth. Commun. 2004, 34, 1729-1736.
13. Denney, D. B.; Ross, S. T. The preparation and reaction of some halophosphoranes. J. Org. Chem. 1962, 27, 998-1000.
14. Speziale, A. J.; Ratts, K. W. Reaction of phosphorus compounds v. resonance-stabilized a-halo-methylenephosphoranes. J. Org. Chem. 1963, 28, 465-469.
15. 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, 2935-2956.
16. Karama, U. One-pot approach to the conversion of alcohols into a-iodo-a, b-unsaturated esters. Synth. Commun. 2010, 40, 3447-3451.
17. Karama, U.; Al-Othman, Z.; Al-Majid, A.; Almansour, A. A facile one-pot synthesis of a-bromo-a,b-unsaturated esters from alcohols. Molecules 2010, 15, 3276-3280.
18. Kayser, M. M.; Zhu, J.; Hooper, D. L. Stabilized haloylides: Synthesis and reactivity. Can. J. Chem. 1997, 75, 1315-1321.