Tetrahedron Letters p. 545 - 548 (1981)
Update date:2022-08-05
Topics:
Bailey, William F.
Croteau, Allan A.
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 C-O bond, and only minor amounts of the expected 2-R-1,3-dioxanes.
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