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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Radical addition to oxime ethers for asymmetric synthesis of beta-amino acid derivatives
Hideto Miyabe1, Kayoko Fujii, Takeaki Naito
1Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.
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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