131074-33-4Relevant academic research and scientific papers
[1,4]-SPh shift cyclisations or [1,2]-SPh-cyclisations as alternative cascade sequences for stereocontrolled synthesis of substituted tetrahydrofurans
Eames, Jason,Kuhnert, Nikolai,Warren, Stuart
, p. 1215 - 1218 (1999)
Treatment of 4-phenylsulfanyl-1,5,7-triols with TsCl in pyridine gives substituted tetrahydrofurans by [1,4]-SPh participation via a five membered sulfonium salt and then capture by a tethered nucleophile. Acid catalysed rearrangement gives other THFs by [1,2]-SPh migration and cyclisations.
The scope and limitation of the [1,4]-SPh shift in the synthesis of allylic alcohols
Aggarwal, Varinder K.,Eames, Jason,De Las Heras, Maria A.,McIntyre, Sara,Warren, Stuart
, p. 4456 - 4461 (2007/10/03)
Treatment of a series of 4-phenylsulfanyl-1,3-diols with toluene-p-sulfonyl chloride in pyridine gives stereospecifically substituted allylic alcohols in near quantitative yield via a [1,4]-SPh shift. We comment on the structural variation at both the mig
STEREOELECTRONIC FACTORS IN THE SYNTHESIS OF TETRAHYDROFURANS BY HYDROXYL PARTICIPATION IN PHENYLTHIO MIGRATION
McIntyre, Sara,Warren, Stuart
, p. 3457 - 3460 (2007/10/02)
The factors controlling the title reaction were investigated with two tethered hydroxyl nucleophiles and include preferential attack at the more highly substituted carbon atom, preferential formation of the more highly substituted five-membered ring, and
