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

文献情報

出版日 2002-12-16

DOI 10.1039/B208823A

インパクトファクター 3.876

著者

Hideto Miyabe, Kayoko Fujii, Takeaki Naito

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要旨

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.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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

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