Radical addition to oxime ethers for asymmetric synthesis of β-amino acid derivatives

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Abstract
The diastereoselective alkyl radical addition to chiral oxime ethers was studied with a view to preparing enantiomerically pure α,β-dialkyl-β-amino acid derivatives. The phase transfer-catalyzed alkylation of Oppolzer's camphorsultam derivative of oxime ether proceeded smoothly to give the alkylated N-(β-oximino)acyl derivatives. In the presence of BF3·OEt2, radical addition to the oxime ethers proceeded using triethylborane as the radical initiator to give α,β-dialkyl-β-amino acid derivatives with excellent diastereoselectivity.

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