The generation of a new Lewis acid (BF 2 OBn · OEt 2 ) has been reported, and its usefulness has been demonstrated in the regio‐ and stereoselective ring‐opening of trisubstituted epoxides. This Lewis acid is one in a series of new Lewis acids generated from BF 3 · OEt 2 that display varying levels of Lewis acidity. When paired with a modified Shi epoxidation protocol, highly functionalized propionate units, such as those found in a wide variety of natural products, can be accessed. In conjunction with a Mukaiyama oxidative cyclization employing our second generation catalyst Co(nmp) 2 , this procedure ultimately culminated in the shortest and highest yielding route towards the methyl‐substituted trans ‐tetrahydrofuran ( trans ‐THF) fragment present in amphidinolide C, C2, and F.
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Morra et al. (2012) studied this question.
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