Abstract
Stereoelectronic factors are apparently responsible for the high selectivity observed in the title SN1-type reaction of acetates 1 in favor of the anti products 2. The preferred conformation of the intermediate propargylic cations would lead to the syn product; however, a second conformation exists, in which the tert-butyl group adopts an antiperiplanar orientation with respect to the incoming nucleophile. Tf=trifluoromethanesulfonyl, TMS=trimethylsilyl.
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