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The transformation of methyl 1,2-trans-glycofuranosides to their respective cis-anomers with grignard reagents

โœ Scribed by Masajiro Kawana; Sakae Emoto

Book ID
104245657
Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
120 KB
Volume
19
Category
Article
ISSN
0040-4039

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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)-0(1) bond remote from the 4-methyl substituent. The analogous r-2-methoxy-cis-4,cis-6-dimethyi-l,3dioxane (2) is totally inert to the acti

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The Stereochemistry of the Grignard -Ortho Ester Reaction Revisited: Regioselective Endocyclic Cleavage in the Reaction of Grignard Reagents with cis-2-Methoxy-4-methyl-1,3-dioxane. -cis-Dioxane (Ia) selectively reacts with Grignard reagents (cf. (II)) via rupture of the less congested C(2)-O(1) bo