Synthesis of 1',3'-dioxolan-2'-one by the reaction of steroidal oxiranes with carbon dioxide: Synthesis of five-membered cis cyclic carbonates

Synthetic Communications

Volumn 40, Issue 15, 2010, Pages 2278-2283

  Shamsuzzaman, ^a   Baqi, Khan Aaftab Alam Abdul ^a  

^a ALIGARH MUSLIM UNIVERSITY   (India)

Author keywords

Carbon dioxide; dimethyl formamide; dioxolan 2' one (dioxolanone); sodium bromide; steroidal epoxide

Indexed keywords

1',3' DIOXOLAN 2' ONE; 3BETA ACETOXY 5,6ALPHA EPOXY 5ALPHA CHOLESTANE; 3BETA ACETOXY 5ALPHA CHOLESTAN [5,6ALPHA DEXTRO] 1',3 'DIOXOLAN 2' ONE; 3BETA CHLORO 5,6ALPHA EPOXY 5ALPHA CHOLESTANE; 3BETA CHLORO 5ALPHA CHOLESTAN [5,6ALPHA DEXTRO] 1',3 'DIOXOLAN 2' ONE; 5,6ALPHA EPOXY 5ALPHA CHOLESTANE; 5ALPHA CHOLESTAN [5,6ALPHA DEXTRO] 1',3 'DIOXOLAN 2' ONE; BROMIDE ION; CARBON DIOXIDE; CARBONIC ACID; CHOLESTANE DERIVATIVE; ETHYLENE OXIDE; ETHYLENE OXIDE DERIVATIVE; SODIUM BROMIDE; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERIC PRESSURE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED RADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE MEASUREMENT;

EID: 77954463684     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903221761     Document Type: Article

References (29)

1. Takeshi, I.; Nobuhira, K.; Takeshi, E. Reaction of various oxiranes and carbon dioxide: Synthesis and aminolysis of five-membered cyclic carbonates. Bull. Chem. Soc. Jpn. 2000, 73, 713-719;
2. Hough, L.; Priddle, J. E.; Theobald, R. S. The carbonates and thiocarbonates of carbohydrates. Adv. Carbohydr. Chem. 1960, 15, 91-158.
3. Amarnath, V.; Broom, A. D. Chemical synthesis of oligonucleotides. Chem. Rev. 1977, 77, 183-217.
4. Gigg, J.; Gigg, R. 1-O-Benzyl-L-glycerol and-D-(glycerol 1,2-carbonate). J. Chem. Soc. C 1967, 17, 1865-1866;
5. Gigg, J.; Gigg, R. The preparation of unsymmetrical diglycerides. J. Chem. Soc. C 1967, 17, 431-434.
6. Letsinger, R. L.; Ogilvie, K. K. Use of p-nitrophenyl chloroformate in blocking hydroxyl groups in nucleosides. J. Org. Chem. 1967, 32, 296-300.
7. Konig, W. A.; Steinbach, E.; Ernst, K. Phosgene as a reagent for the enantiomeric resolution of 1,2-and 1,3-diols, a-amino alcohols, a-hydroxy acids, and N-methyl-a-amino acids by gas chromatography. Angew. Chem., Int. Ed. Engl. 1984, 23, 527-528.
8. Tatsuta, K.; Akimoto, K.; Annaka, M.; Ohno, Y.; Kinoshita, M. Enantiodivergent total synthesis of nanaomycins and their enantiomers, kalafungins. Bull. Chem. Soc. Jpn. 1985, 58, 1699-1706.
9. Trost, B. M.; Chan, D. M. T. Synthesis of 4-methylene-1,3-dioxolan-2-one: A bifuntional cyclic carbonate. J. Org. Chem. 1983, 48, 3346-3347.
10. 2 adducts employed in the synthesis of carboxylates and a-alkyli-dene cyclic carbonates. Tetrahedron Lett. 2009, 50, 104-107.
11. Bhusan, V.; Chakraborty, T. K.; Chandrasekaran, S. Formation of cyclic carbonates in the reaction of 1,2-ditertiary diols with acetic anhydride an 4-(dimethylamino) pridine. J. Org. Chem. 1984, 49, 3974-3978.
12. Roush, W. R.; Hagadorn, S. M. Synthesis of mycarose and epi-axenose from non-carbohydrate precursors. Carbohydr. Res. 1985, 136, 187-193.
13. Nicolaou, K. C.; Webber, S. E. A general strategy for the total synthesis of the presumed lipoxin structures. J. Chem. Soc., Chem. Commun. 1985, 297-301.
14. Venturello, C.; D'Aloisio, R. A convenient synthesis of 1,2-alkanediyl carbonates. Synthesis 1985, 33-34.
15. 2 with enantiopure amino epoxides under mild conditions: Synthesis and synthetic applications of enantiopure (4R, 1S)-or (4S, 1S)-4-(1-aminoalkyl)- 2-oxo-1,3-dioxolanes. J. Org. Chem. 2007, 72, 7567-7573.
16. Pasquale, R. J. D. Unusual catalysis nickel(0) complexes. J. Chem. Soc., Chem. Commun. 1973, 157-158.
17. Takeda, N.; Inoue, S. Activation of carbon dioxide by tetraphenylporphinatoaluminium methoxide: Reaction with epoxide. Bull. Chem. Soc. Jpn. 1978, 51, 3564-3567.
18. Matsuda, H.; Ninagawa, A.; Nomura, R.; Tsuchida, T. Reaction of carbon dioxide with epoxides in the presence of organotin compounds. Chem. Lett. 1979, 8, 573-574.
19. Matsuda, H.; Ninagawa, A.; Nomura, R. Reaction of carbon dioxide with epoxides in the presence of pentavalent organoantimony compounds. Chem. Lett. 1979, 8, 1261-1262.
20. Aida, T.; Inoue, S. Activation of carbon dioxide with aluminum porphyrin and reaction with epoxide: Studies on (tetraphenylporphinato)aluminum alkoxide having a long oxyalkylene chain as the alkoxide group. J. Am. Chem. Soc. 1983, 105, 1304-1309.
21. Lu, X. B.; Zhang, Y. J.; Liang, B.; Xiao, L.; Wang, H. Chemical fixation of carbon dioxide to cyclic carbonates under mild conditions with highly active bifunctional catalysts. J. Mol. Cat. A 2004, 210, 31-34.
22. Nomura, R.; Ninagawa, A.; Matsuda, H. Synthesis of cyclic carbonates from carbon dioxide and epoxides in the presence of organoantimony compounds as novel catalysts. J. Org. Chem. 1980, 45, 3735-3738.
23. Fujinami, T.; Suzuki, T.; Kamiya, M.; Fukuzawa, S.; Sakai, S. Palladium-catalyzed reaction of butadiene monoxide with carbon dioxide. Chem. Lett. 1985, 14, 199-200.
24. Baba, A.; Nozaki, T.; Matsuda, H. Carbonate formation from oxiranes and carbon dioxide catalyzed by organotin halide-tetraalkylphosphonium halide complexes. Bull. Chem. Soc. Jpn. 1987, 60, 1552-1554.
25. 2 and propargyl alcohols catalyzed by metal salts under mild conditions. J. Org. Chem. 2004, 69, 391-394.
26. Nobuhira, K.; Nobutaka, H.; Takeshi, E. Catalytic activity of various salts in the reaction of 2,3-epoxypropyl phenyl ether and carbon dioxide under atmospheric pressure. J. Org. Chem. 1993, 58, 6198-6202.
27. Yano, T.; Matsui, H.; Koike, T.; Ishiguro, H.; Fujihara, H.; Yoshihara, M.; Maeshima, T. Magnesium oxide-catalysed reaction of carbon dioxide with an epoxide with retention of stereochemistry. Chem. Commun. 1997, 1129-1130.
28. Banerji, A.; Chatterjee, A.; Saha, M.; Dhara, K. P.; Kanrar, S.; Mukherjee, P.; Neuman, A.; Prange, T. Reactions and rearrangements of triterpenoids-3-epitaraxerol and its transformation products. Indian J. Chem. 1999, 38B, 1322-1330;
29. Henbest, H. B.; Wringley, T. I. Aspect of stereochemistry, part IX: The formation of fluorohydrins from the cholesterol 5:6-epoxides and boron trifluoride-ether complex. J. Chem. Soc. 1957, 4765-4768.