Secondary and tertiary alcohols as nucleophiles in the stereospecific synthesis of substituted tetrahydrofurans by cyclisation of 1,3-diols with phenylsulfanyl migration

Tetrahedron Letters

Volumn 37, Issue 23, 1996, Pages 4077-4080

  Eames, Jason ^a   De Las Heras, Maria A ^a   Warren, Stuart ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029981005     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00737-X     Document Type: Article

References (13)

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7. Eames, J.; Heras, M. A. d. I.; Jones, R. V. H.; Warren, S. Tetrahedron Lett, 1996, 37, 1117-1120.
8. Eliel, E. L.; Pearson, W. H.; Jewell, L. M.; Abatjoglou, A. G.; Kenan, W. R. Tetrahedron Lett., 1980, 21, 331-334.
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11. Eames., J.; de las Heras, M.; Warren, S. in preparation.
12. 13 of drawing the chain or ring in its best conformation and noting the relationship between the two most important groups, such as the two OH groups in 21. This arbitrary method becomes particularly so with compounds 31 and 32. It seems most helpful to use the two OH groups in 31 but the PhS and Ph groups in 32.
13. Masamune, S.; Kaiho, T.; Garvey, D. S. J. Am. Chem. Soc., 1982, 104, 5521-5523.