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ChemInform Abstract: Efficient and Stereospecific Construction of Asymmetric Quaternary Carbons via γ-Alkyl-γ,δ-epoxy Acrylates.

✍ Scribed by N. ISHIBASHI; M. MIYAZAWA; M. MIYASHITA

Book ID
101867240
Publisher
John Wiley and Sons
Year
2010
Weight
36 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Efficient and Stereospecific Construction of Asymmetric Quaternary Carbons via γ-Alkyl-γ,δ-epoxy Acrylates.

-The methylation of epoxy acrylates with Me 3 Al (II) is investigated. Thus, the trans compound (I) reacts with an excess of (II) in the presence of water to form the syn compound (III) as single product. Similarly, the cis-epoxy ester (IV) leads to the anti compound (V) exclusively. On the other hand, the ester (VI), lacking the double bond, reacts with Me 3 Al under similar conditions to yield the product (VII) of exclusive β-methylation.

-(ISHIBASHI, N.; MIYAZAWA, M.;

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