Abstract
The tris(dimethylamido)sulfonium difluorotrimethylsilicate (TAS-TMSF 2) mediated reaction of dialkyl substituted trimethylsilyl ketene acetals 4 or 6 with aldonolactones 1, 9 or 11 affords dimers 8, 10 and 12 in an unprecedented but diastereoselective manner. In addition, under the same conditions the reaction of a suitable protected aldonolactone with a cyclic trimethylsilyl ketene acetal 14 results in a diastereoselective chain elongation thus creating two new stereogenic centers diastereoselectively.
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