Tetrahedron letters

The stereochemistry of the Grignard—Ortho ester reaction revisited: Regioselective endocyclic cleavage in the reaction of Grignard reagents with cis-2-methoxy-4- …

WF Bailey, AA Croteau, AD Rivera

Index: Bailey, William F.; Croteau, Allan A.; Rivera, Alberto D. Tetrahedron Letters, 1997 , vol. 38, # 23 p. 4047 - 4050

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Citation Number: 2

Abstract

The reaction of cis-2-methoxy-4-methyl-1, 3-dioxane (4) with Grignard reagents proceeds in a totally regioselective manner via rupture of the less congested C (2) O (1) bond remote from the 4-methyl substituent. The analogous r-2-methoxy-cis-4, cis-6-dimethyl-1, 3-dioxane (2) is totally inert to the action of Grignard reagents.

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