Facile Retro-[1,4]-Brook Rearrangement of a [(2-Siloxycyclopentyl)methyl]lithium Species
β Scribed by Jiang, Xing-Long; Bailey, William F.
- Book ID
- 126325831
- Publisher
- American Chemical Society
- Year
- 1995
- Tongue
- English
- Weight
- 469 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0276-7333
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π SIMILAR VOLUMES
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
The retro-[1,4]-Brook rearrangement (also referred to as the West or silyl-Wittig rearrangement) has been employed with acetophenone silyl enol ethers to allow regiospecific migration of the silicon from oxygen to the ortho position of the aromatic ring. The enolate that results from this process ma