Abstract
The stereoelectronically controlled reaction of 2-methoxy-1,3-dioxane ( 1 ) with Grignard reagents does not follow the course suggested by the behavior of anancomeric models for the conformational isomers of 1 . Treatment of 1 with RMgX leads to the predominant formation of acid labile 3-(1′-methoxyalkoxy)-1-propanols, derived from endocyclic cleavage of the ring CO bond, and only minor amounts of the expected 2-R-1,3-dioxanes.
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