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1,3-ASYMMETRIC INDUCTION IN RETRO-[1,4]-BROOK REARRANGEMENTS OF LITHIATED ALLYL METHYL ETHERS AND LITHIATED ALLYL MOM ETHERS

✍ Scribed by Dirk Goeppel; Reinhard Brückner

Book ID: 104256882
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 281 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00517-0

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✦ Synopsis

The tBrrPh*Si-containing allyl methylether cis-2 and its trans isomerwere Iithiatedwith sBuLi at -78°C in THF. Thereupon,diastereoselectiveretro-[l,4]-Brook rearrangementsoccurred which furnishedthe allylsilanearrti,trans-5 with 86-87%diastereocontrol. The analogousallylMOM etherscis-and rrans-3 underwentsimilarretro-[1,4]-Brookrearrangementsupontreatmentwith sBuLi.They yieldedthe allylsilaneunti,trarrs-6with 80-82%diastereoselectivity. @ 1997E1sevier ScienceLtd.

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