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膦催化的乙烯基吡啶氮杂-MBH 反应:高效快速构建 2,3,5-三芳基取代的 3-吡咯啉。

Phosphine-Catalyzed Aza-MBH Reactions of Vinylpyridines: Efficient and Rapid Access to 2,3,5-Triarylsubstituted 3-Pyrrolines.

机构信息

†State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.

‡Shanghai Key Laboratory of New Drug Design, School of Pharmacy, and State Key Laboratory of Bioengineering Reactor, East China University of Science and Technology, 130 Mei-long Road, Shanghai 200237, China.

出版信息

Org Lett. 2015 May 1;17(9):2214-7. doi: 10.1021/acs.orglett.5b00811. Epub 2015 Apr 16.

Abstract

Vinylpyridines have been developed in aza-Morita-Baylis-Hillman (MBH) reaction to construct triarylsubstituted 3-pyrrolines. The first electron-deficient aromatic ring is marked as an activating mode for the vinyl group in the MBH reaction. This method provides efficient and rapid access to a range of triarylpyrrolines in good yields and at an excellent level of diastereoselectivity. Moreover, the synthetic potential of this protocol is further enhanced by the straightforward synthesis of unsymmetrical tri- and polyarylsubstituted pyrroles.

摘要

已在氮杂-Morita-Baylis-Hillman(MBH)反应中开发了乙烯基吡啶,以构建三芳基取代的 3-吡咯啉。第一个缺电子芳环被标记为 MBH 反应中乙烯基的活化模式。该方法以高产率和极好的非对映选择性提供了一系列三芳基吡咯啉的有效和快速途径。此外,通过直接合成不对称的三芳基和多芳基取代的吡咯,进一步增强了该协议的合成潜力。

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