Diastereoselective synthesis of 1,2-O-isopropylidene-1,6-dioxaspiro[4,4]nonane applying the methodology of generation of radical cations under non-oxidizing conditions

Tetrahedron Letters

Volumn 44, Issue 20, 2003, Pages 3919-3921

  Sartillo Piscil, Fernando ^a   Vargas, Mónica ^a   Anaya De Parrodi, Cecilia ^b   Quintero, Leticia ^a  

^a BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

^b UNIVERSIDAD DE LAS AMÉRICAS PUEBLA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 O ISOPROPYLIDENE 1,6 DIOXASPIRO[4,4]NONANE; ALKANE DERIVATIVE; ALKENE; CATION; OXIDIZING AGENT; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG SYNTHESIS; HYDROGEN ABSTRACTION REACTION; METHODOLOGY; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0037433836     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00817-7     Document Type: Article

References (18)

1. Crich D. Renaud P., Sibi M. Radicals in Organic Synthesis. 2:2001;188-206 Wiley-VCH, Weinheim, Huang, X. Ph.D. Dissertation, University of Illinois at Chicago, 2000.
2. Pogozelski W.K., Tullius T.D. Chem. Rev. 98:1998;1089-1107.
3. Crich D., Huang X., Newcomb M. Org. Lett. 1:1999;225-228.
4. Crich D., Huang X., Newcomb M. J. Org. Chem. 65:2000;523-529.
5. Crich D., Ranganathan K., Huang X. Org. Lett. 3:2001;1917-1919.
6. Crich D., Neelamkavil S. Org. Lett. 4:2002;2573-2575.
7. Crich D., Ranganathan K. J. Am. Chem. Soc. 124:2002;12422-12423.
8. Crich D., Huang W. J. Am. Chem. Soc. 123:2001;9239-9245.
9. Perron F., Albizati K.F. Chem. Rev. 89:1989;1617-1661.
10. Kaiser R. Chimia. 54:2000;346-363.
11. 3) δ 24.2, 26.1, 26.6, 28.5, 62.3, 75.0, 80.7, 82.2, 85.3, 104.2, 111.4.
12. Mitsunobu O. Synthesis. 1981;1.
13. 2O and extracted with ethyl acetate and the residue was purified by flash chromatography.
14. Harcken C., Martin S.F. Org. Lett. 3:2001;3591-3593.
15. Valverde S., Martin-Lomas M., Herradon B., Garcia-Ochoa S. Tetrahedron. 43:1987;1895-1901.
16. Corey E.J., Goto G. Tetrahedron Lett. 21:1980;3463-3466.
17. Kim S., Lee T.A., Song Y. Synlett. 1998;471-472.
18. 4: C, 59.98; H, 8.05. Found C, 60.23; H, 8.21%.