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Volumn 68, Issue 5, 2003, Pages 1821-1826

Efficient desymmetrization of "pseudo"-C2-symmetric substrates: Illustration in the synthesis of a disubstituted butenolide from arabitol

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CYCLIZATION;

EID: 0037424310     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026696r     Document Type: Article
Times cited : (21)

References (89)
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    • During the course of this work, an example of a similar symmetry-breaking tactic was published: Hale, K. J.; Hummersone, M. G.; Bhatia, G. S. Org. Lett. 2000, 2, 2189-2192.
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    • (c) After our initial studies in the area, the protection of arabitol in DMF as solvent (12 h, rt) was reported to yield the 1,2:4,5-bis-acetonide, although no detailed experimental was given (Terauchi, T.; Terauchi, T.; Sato, I.; Tsukada, T.; Kanoh, N.; Nakata, M. Tetrahedron Lett. 2000, 41, 2649-2653.
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    • 1H NMR was very straightforward: the secondary hydroxyl group of the desired isomer 5 appeared as a doublet at 2.30 ppm, while the primary alcohol proton of the thermodynamic isomer 6 appeared as a doublet of doublets at 2.34 ppm. In addition, the observed 13C NMR chemical shift values for the isopropylidene acetal- and methyl carbons correlated well with the general chemical shift regions reported for five-membered acetonides: Buchanan, J. G.; Chacón-Fuertes, M. E.; Edgar, A. R.; Moorhouse, S. J.; Rawson, D. I.; Wightman, R. H. Tetrahedron Lett. 1980, 21, 1793-1796. Buchanan, J. G.; Edgar, A. R.; Rawson, D. I.; Shahidi, P.; Wightman, R. H. Carbohydr. Res. 1982, 100, 75-86.
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    • 1H NMR was very straightforward: the secondary hydroxyl group of the desired isomer 5 appeared as a doublet at 2.30 ppm, while the primary alcohol proton of the thermodynamic isomer 6 appeared as a doublet of doublets at 2.34 ppm. In addition, the observed 13C NMR chemical shift values for the isopropylidene acetal- and methyl carbons correlated well with the general chemical shift regions reported for five-membered acetonides: Buchanan, J. G.; Chacón-Fuertes, M. E.; Edgar, A. R.; Moorhouse, S. J.; Rawson, D. I.; Wightman, R. H. Tetrahedron Lett. 1980, 21, 1793-1796. Buchanan, J. G.; Edgar, A. R.; Rawson, D. I.; Shahidi, P.; Wightman, R. H. Carbohydr. Res. 1982, 100, 75-86.
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    • Wiley: New York; Chapters 3 and 5
    • Permutation of two ligands of the double bond does not lead to a stereoisomer. For a clear discussion about stereogenicity/chirotopicity, see: (a) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; Chapters 3 and 5, pp 53 and 123.
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    • note
    • Both a single carbon and an olefinic double bond (axis) can be stereogenic elements. See ref 19a, pp 52-53 and 1208, and ref 19b, pp 11-13.
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    • note
    • 2-symmetric if it did not contain a central chirotopic, nonstereogenic double bond (axis).
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    • note
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    • Napolitano, E.; Fiaschi, R.; Mastrorilli, E. Synthesis 1986, 122-125. The preparation was slightly modified: CSA was used instead of p-TsOH, and 5 equiv of methanol was used instead of 15 equiv. We found that it was important to purify the 3,3-dimethoxypentane by fractional distillation (bp 125 °C, atmospheric pressure) before use in the protection reaction.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.