Abstract

An efficient protocol for stereoselective construction of densely functionalized pyrrolidines by a [3+2]-annulation reaction of N-tosyl-α-amino aldehydes and 1,3-bis(silyl)propenes is described. This methodology is also applied as a key step in the synthesis of the polyhydroxylated pyrrolidine alkaloid 2,5-dideoxy-2,5-imino-d-glucitol (DGDP).

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