Reaction of 2-methoxy-1, 3-dioxane with grignard reagents: reagent-substrate complexation and stereoelectronic control.

WF Bailey, AA Croteau

Index: Bailey, William F.; Croteau, Allan A. Tetrahedron Letters, 1981 , vol. 22, p. 545 - 548

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Citation Number: 8

Abstract

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