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

N. Satyamurthi; Jaimala Singh; Indrapal Singh Aidhen

doi:10.1055/s-2000-6337

Synthesis 2000; 2000(3): 375-382
DOI: 10.1055/s-2000-6337

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

N. Satyamurthi^* , Jaimala Singh, Indrapal Singh Aidhen

^*Department of Chemistry, Indian Institute of Technology, Madras, Chennai-600 036, India; Fax +91 (44) 2 35 05 09; E-mail: isingh@pallava.iitm.ernet.in

Abstract

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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 ^ΘCH₂CHO and ^ΘCH₂COR 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

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