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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Doi:10.1021/acs.jafc.0c04500
(2020)Doi:10.1039/P19810000712
(1981)Doi:10.1021/ja3100963
(2013)Doi:10.1016/S0040-4020(01)86182-2
(1988)Doi:10.1016/j.carres.2004.07.012
(2004)Doi:10.1039/b506131h
(2005)
