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A highly diastereoselective approach for the synthesis of protected α,β-dioxyaldehydes derived from ( Z )-tris(trimethylsilyl)silyl "super silyl" enol ethers is described. A general and highly syn -stereoselective aldol reaction directed by the "super silyl" group catalyzed by triflimide (HNTf 2 ) is developed providing α,β-dioxyaldehydes and 1,2,3-triol fragments which can be a useful platform for the elaboration of natural and unnatural sugar derivatives.

A highly diastereoselective “super silyl” governed aldol reaction: synthesis of α,β-dioxyaldehydes and 1,2,3-triols