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Synlett 2000; 2000(7): 1073-1075
DOI: 10.1055/s-2000-6687
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Chelation-Controlled 1,3-Asymmetric Induction in the Radical Addition-Allylation Reactions of 4-Hydroxy- and 4-Alkoxy-2-methylenecarboxylic Esters

Hajime Nagano* , Tamano Hirasawa, Tomoko Yajima
  • *Department of Chemistry, Faculty of Science, Ochanomizu University, Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan; Fax +81-3-59 78-58 98; E-mail: nagano@cc.ocha.ac.jp
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Publication Date:
31 December 2000 (online)

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The radical reaction of ethyl 4-methoxymethoxy-2-methylenealkanoates with ethyl iodide and allyltributyltin in the presence of MgBr2 gave exclusively ethyl (2R*,4R*)-2-allyl-4-methoxymethoxy-2-propylalkanoates in good yields, whereas the reaction of ethyl 4-hydroxy-2-methylenealkanoates performed in the presence of Et2AlCl gave exclusively (2S*,4R*)-4-alkyl-2-allyl-2-propyl-4-butanolides in good yields. The diastereoselectivities in the radical reaction of 4-phenyl-substituted esters were moderate to good.

radical reaction - 1,3-asymmetric induction - chelation control - quaternary carbon center