Synthesis and Application of N-Methoxy-N-methyl-2-phenylsulfonylacetamide as a Two-Carbon Homologating Agent

All articles of this category With the well-known precedence that N -methoxy- N -methyl amides are excellent acyl cation and aldehyde equivalents, N -methoxy- N -methyl-2-phenylsulfonylacetamide ( 3 ), a new reagent, synthetically equivalent to Θ CH 2 CHO and Θ CH 2 COR was synthesised. The simplicity involved in the alkylation at the active methylene site in 3 , followed by safe removal of the phenylsulfonyl group, makes 3 a versatile reagent for two-carbon homologation of alkyl halides. The method, when applied to sugar halides 6j and 6k led to the synthesis of 2,3-dideoxy sugars. Weinreb amides - two-carbon homologation - higher 2,3-dideoxy sugars - (+)-aspicillin - sulfones - desulfonylation - alkylations