ChemInform Abstract: 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.

✍ Scribed by W. F. BAILEY; A. A. CROTEAU; A. D. RIVERA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 29 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199737096

✦ Synopsis

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) bond remote from the 4-methyl substituent. The corresponding dimethyl derivative (Ib) is totally inert to Grignard reagents.