Ni-Catalyzed chemoselective alcoholysis of N-acyloxazolidinones,Green Chemistry

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Ni-Catalyzed chemoselective alcoholysis of N-acyloxazolidinones
Green Chemistry ( IF 9.3 ) Pub Date : 2018-01-05 00:00:00 , DOI: 10.1039/c7gc03534a
Pei-Qiang Huang _{1,

2,

3,

4,

5} , Hui Geng _{1,

2,

3,

4,

5}

Affiliation

Although N-acyloxazolidinone-based (catalytic) asymmetric synthetic methodologies occupy an important position in modern organic synthesis, the catalytic cleavage of a chiral auxiliary remains underdeveloped. We report the Ni(cod)₂/bipyr.-catalyzed alcoholysis of N-acyloxazolidinones to deliver esters. The reaction is broad in scope for both N-acyloxazolidinone substrates and alcohol nucleophiles, and displays good functional group tolerance and excellent chemoselectivity. A gram-scale methanolysis allowed the enantioselective synthesis of the C22–C26 segment of a close analogue of the potent immunosuppressant agent FK506.

中文翻译：

Ni催化的N-酰基恶唑烷酮的化学选择性醇解

尽管基于N-酰基氧杂唑烷酮的（催化）不对称合成方法在现代有机合成中占有重要地位，但手性助剂的催化裂解仍未开发。我们报告了N（酰基）xx恶唑烷酮的Ni（cod）_{2 /}联吡啶催化的醇解反应以递送酯。该反应对于N-酰基氧杂唑烷酮底物和醇亲核试剂都具有广泛的范围，并且显示出良好的官能团耐受性和优异的化学选择性。克级的甲醇分解作用可以使强效免疫抑制剂FK506的紧密类似物的C22–C26片段进行对映选择性合成。

更新日期：2018-02-06

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