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ChemInform Abstract: Chelation-Controlled 1,3-Asymmetric Induction in Radical Addition to γ-Hydroxy- and γ-Alkoxy-α-methylenecarboxylic Esters.

✍ Scribed by Hajime Nagano; Satoko Toi; Tomoko Yajima


Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis


1999 hydroxycarboxylic acids hydroxycarboxylic acids (ether carboxylic acids) (acyclic compounds) and esters P 0280

19 -084

Chelation-Controlled 1,3-Asymmetric Induction in Radical Addition to γ-Hydroxy-and γ-Alkoxy-α-methylenecarboxylic Esters.

γ-Oxy-α-methylenecarboxylic esters react with the organic iodides (II) under radical conditions in the presence of mild Lewis acids. Isopropyl or cyclohexyl iodide give the syn-adducts (III) predominantly, whereas tert-butyl iodide affords the anti-adducts (IV) preferentially. -(NAGANO, HAJIME; TOI,


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