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An improved protocol for the Prins desymmetrisation of cyclohexa-1,4-dienes

✍ Scribed by Michael Butters; Mark C. Elliott; Joseph Hill-Cousins; James S. Paine; Alexander W.J. Westwood

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
171 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

Improved conditions are reported for the Prins-pinacol rearrangement of cyclohexa-1,4-diene-derived acetals. The use of triflic acid gives particularly clean reaction, resulting in a mixture of regioisomers in an approximately 10:1 ratio. A tethered version of this reaction is also reported, giving a tricyclic compound with the same stereochemistry as the core of the cladiellin diterpenes.

πŸ“œ SIMILAR VOLUMES

Diastereospecific Tandem Prins Cyclisati
Diastereospecific Tandem Prins Cyclisation/Rearrangement Reactions for the Desymmetrisation of Cyclohexa-1,4-dienes
✍ Mark C. Elliott; Nahed N. E. El Sayed; James S. Paine πŸ“‚ Article πŸ“… 2007 πŸ› John Wiley and Sons 🌐 English βš– 275 KB πŸ‘ 1 views

## Abstract The Prins cyclisation has been used for the first time to desymmetrise a 1,4‐diene. Products derived from both normal Prins and rearrangement pathways were obtained, all with complete stereocontrol. (Β© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)