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  • Title: Radical addition to oxime ethers for asymmetric synthesis of beta-amino acid derivatives.
    Author: Miyabe H, Fujii K, Naito T.
    Journal: Org Biomol Chem; 2003 Jan 21; 1(2):381-90. PubMed ID: 12929434.
    Abstract:
    The diastereoselective alkyl radical addition to chiral oxime ethers was studied with a view to preparing enantiomerically pure alpha,beta-dialkyl-beta-amino acid derivatives. The phase transfer-catalyzed alkylation of Oppolzer's camphorsultam derivative of oxime ether proceeded smoothly to give the alkylated N-(beta-oximino)acyl derivatives. In the presence of BF3.OEt2, radical addition to the oxime ethers proceeded using triethylborane as the radical initiator to give alpha,beta-dialkyl-beta-amino acid derivatives with excellent diastereoselectivity.
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