[1,4]-SPh shift cyclisations or [1,2]-SPh-cyclisations as alternative cascade sequences for stereocontrolled synthesis of substituted tetrahydrofurans

Synlett

Volumn , Issue 8, 1999, Pages 1215-1218

  Eames, Jason ^a,c   Kuhnert, Nikolai ^b,c   Warren, Stuart ^c  

^a QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

^b UNIVERSITY OF SURREY   (United Kingdom)

^c UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Cyclisations; Heterocycles; Rearrangements; Stereoselective synthesis; Sulfur chemistry

Indexed keywords

TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032769889     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2815     Document Type: Article

References (17)

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8. Protection of 4-hydroxy-pentan-2-one turned out in our hands to be very capricious, since formation of a silylated cyclic five-membered acetal, resulting from a highly favourable 5-exo-tet process, was a competing reaction. Protection was achieved by extremely slow addition of TBDPSCl to a stirred solution of the alcohol in DMF/imidazole and stirring for 14 days.
9. (a) Groot, A. d.; Jansen, B. J. M. Synthesis 1985, 434.
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14. As an alternative product, an eight membered ring resulting from a 8-exo-tet cyclisation, would be feasible but could be excluded by MS data.
15. Baldwin, J. E. J. Chem. Soc. Chem. Commun. 1976, 734. Attempted stereoselective [1,4]-PhS migration on the triol 29 gave a 1:1 mixture of the two products of a [1,4]-SPh shift, syn- and anti-30, and about 30% of the product of a [1,2]-SPh shift, the THF anti-31 (equation presented) Scheme 7
16. Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066.
17. 3) 136.5, 128.8, 128.6, 125.7 (SPh), 87.1 (C-O), 82.6 (CO), 82.0 (CHOH), 44.2 (CSPh), 34.7, 32.2, 28.1 and 25.6; m/z 280 (2%, M) and 110 (30, PhS).