Abstract
The tBuPh 2Si-containing allyl methyl ether cis- 2 and its trans isomer were lithiated with sBuLi at −78°C in THF. Thereupon, diastereoselective retro-[1,4]-Brook rearrangements occurred which furnished the allylsilane anti,trans- 5 with 86–87% diastereocontrol. The analogous allyl MOM ethers cis- and trans- 3 underwent similar retro-[1,4]-Brook rearrangements upon treatment with sBuLi. They yielded the allylsilane anti,trans- 6 with 80–82% diastereoselectivity. © 1997 Elsevier Science Ltd.
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