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Base catalysed rearrangements of 4-hydroxyphenyl allyl ethers: syntheses of alliodorin and alliodorol

✍ Scribed by Harwood, Laurence M.; Oxford, Anona J.; Thomson, Colin


Book ID
120987852
Publisher
The Royal Society of Chemistry
Year
1991
Tongue
English
Weight
262 KB
Volume
18
Category
Article
ISSN
0022-4936

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1,3-ASYMMETRIC INDUCTION IN RETRO-[1,4]-
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The tBrrPh\*Si-containing allyl methylether cis-2 and its trans isomerwere Iithiatedwith sBuLi at -78Β°C in THF. Thereupon,diastereoselectiveretro-[l,4]-Brook rearrangementsoccurred which furnishedthe allylsilanearrti,trans-5 with 86-87%diastereocontrol. The analogousallylMOM etherscis-and rrans-3 un