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Volumn 45, Issue 6, 2004, Pages 1227-1231

Stereoselectivity in the anionic oxy-Cope rearrangement of acyclic vinyl sulfides

Author keywords

Alkenylations; Rearrangements; Stereocontrol; Thioethers

Indexed keywords

ALDEHYDE; ANION; SULFIDE; VINYL DERIVATIVE;

EID: 0742304333     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.132     Document Type: Article
Times cited : (20)

References (32)
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    • Review:
    • Review: Paquette L.A. Tetrahedron. 53:1997;13971-14020.
    • (1997) Tetrahedron , vol.53 , pp. 13971-14020
    • Paquette, L.A.1
  • 3
    • 0041336838 scopus 로고    scopus 로고
    • Recent examples include:
    • Recent examples include: Paquette L.A., Hong F.T. J. Org. Chem. 68:2003;6905-6918.
    • (2003) J. Org. Chem. , vol.68 , pp. 6905-6918
    • Paquette, L.A.1    Hong, F.T.2
  • 9
    • 0038695134 scopus 로고    scopus 로고
    • Review of asymmetric [3,3]-sigmatropic rearrangements:
    • Review of asymmetric [3,3]-sigmatropic rearrangements: Nubbemeyer U. Synthesis. 2003;961-1008.
    • (2003) Synthesis , pp. 961-1008
    • Nubbemeyer, U.1
  • 18
    • 0009594084 scopus 로고
    • A related vinyl sulfone cyclised rather than undergoing AOC rearrangement:
    • A related vinyl sulfone cyclised rather than undergoing AOC rearrangement: Auvray P., Knochel P., Normant J.F. Tetrahedron Lett. 26:1985;4455-4458.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 4455-4458
    • Auvray, P.1    Knochel, P.2    Normant, J.F.3
  • 19
    • 0742307101 scopus 로고
    • Only dihydropyran and cyclohexene derivatives having this functional group relationship have been made previously by cyclodimerisation and Diels-Alder reaction, respectively. Some of the dihydropyrans have antimicrobial properties, while the two functional groups of the cyclohexene derivatives, which are constrained so that intramolecular reaction would give rise to a four membered ring, could been manipulated independently in syntheses of natural products. Examples include:
    • Only dihydropyran and cyclohexene derivatives having this functional group relationship have been made previously by cyclodimerisation and Diels-Alder reaction, respectively. Some of the dihydropyrans have antimicrobial properties, while the two functional groups of the cyclohexene derivatives, which are constrained so that intramolecular reaction would give rise to a four membered ring, could been manipulated independently in syntheses of natural products. Examples include: Stepanova L.G., Keiko N.A., Malkova T.N., Leont'eva A.G., Pushechkina T.Y., Voronkov M.G. Pharm. Chem. J. 22:1988;477-480.
    • (1988) Pharm. Chem. J. , vol.22 , pp. 477-480
    • Stepanova, L.G.1    Keiko, N.A.2    Malkova, T.N.3    Leont'Eva, A.G.4    Pushechkina, T.Y.5    Voronkov, M.G.6
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    • note
    • 18OS requires M, 234.1078.
  • 29
    • 0034674252 scopus 로고    scopus 로고
    • 3,4=9.6-11.6 Hz and COSY and NOE were used to assign the relative stereochemistry and E or Z geometry of each alcohol. For a discussion of conformational effects in open-chain compounds see: Hoffmann R.W. Angew. Chem., Int. Ed. 39:2000;2054-2070.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2054-2070
    • Hoffmann, R.W.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.