Construction of Isoxazolidin‐5‐ones with a Tetrasubstituted Carbon Center: Enantioselective Conjugate Addition Mediated by Phase‐Transfer Catalysis,Advanced Synthesis & Catalysis

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Construction of Isoxazolidin‐5‐ones with a Tetrasubstituted Carbon Center: Enantioselective Conjugate Addition Mediated by Phase‐Transfer Catalysis
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-02-28 , DOI: 10.1002/adsc.201800009
Timothée Cadart ₁ , Vincent Levacher ₁ , Stéphane Perrio ₂ , Jean-François Brière ₁

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An efficient enantioselective Michael reaction of readily available α‐substituted N‐Boc isoxazolidin‐5‐ones is described under phase transfer conditions with up to 95:5 er. The organocatalytic process is promoted by a low catalytic loading of a commercially available N‐spiro quaternary ammonium salt. This sequence opens an entry to chiral heterocyclic platforms displaying a β‐amino carbonyl motif with an α‐all‐carbon quaternary stereogenic center. The methodology was also successfully extended to the asymmetric amination reaction using an azodicarboxylate electrophile.

中文翻译：

用四取代的碳中心构建异恶唑烷-5-酮：相转移催化介导的对映选择性共轭加成反应

描述了在相转移条件下（er最高为95：5 er）容易获得的α-取代的N - Boc异恶唑烷-5-酮的有效对映选择性Michael反应。商用N螺环季铵盐的低催化负荷可促进有机催化过程。该序列打开了一个手性杂环平台的入口，该平台显示了一个具有α-全碳四元立体构象中心的β-氨基羰基基序。该方法还成功地扩展到使用偶氮二羧酸亲电试剂的不对称胺化反应。

更新日期：2018-02-28

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