Since the original discovery of Weinreb [1], that N-methoxy-N-methyl amides 1, now popularly called as Weinreb amides (WA), cleanly reacted with Grignard reagents and organolithium to produce ketones, these amides have gained wide importance as very effective acylating agents for various organometallic reagents The esters and lactones have been invariably converted [5a -g] to Weinreb amides (Scheme 2) by using a combination of trimethyl aluminium and
With the well-known precedence that N-methoxy-N-methyl amides are excellent acyl cation and aldehyde equivalents, Nmethoxy-N-methyl-2-phenylsulfonylacetamide (3), a new reagent, synthetically equivalent to Q CH 2 CHO and Q 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.
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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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