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非稳定型亚甲胺基叶立德参与的三组分1,3-偶极环加成反应合成新型四氢吡咯衍生物 被引量：1

Synthesis of Novel 3,4-Disubstituted Pyrrolidine Derivatives by Three-component 1,3-Dipolar Cycloaddition Reaction by in situ Unstablized Azomethine Ylides
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摘要 N-三甲基硅甲基苄胺和多聚甲醛在磷酸催化下生成非稳定型亚甲胺基叶立德,继而与各种贫电子烯烃在温和条件下发生三组分1,3-偶极环加成反应,高收率合成了10个3,4-二取代四氢吡咯衍生物(其中6个为新化合物),其结构经1H NMR,13C NMR和HR-MS表征。 Ten 3,4-disubstituted pyrrolidine derivatives （six of them were new compounds） in high yield were synthesized by three-component 1,3-dipolar cyeloaddition reaction of electron deficient alkens with unstablized azomethine ylides, which was obtained by the reaction of N-（ trimethylsilylmeth- yl） benzyl-amine with paraformaldehyde in DMF in presence of phosphoric acid. The structures were characterized by 1H NMR, 13C NMR and HR-MS.
作者 潘华 徐亮
机构地区 四川大学华西药学院
出处 《合成化学》 CAS CSCD 北大核心 2012年第4期466-469,共4页 Chinese Journal of Synthetic Chemistry
基金 国家自然科学基金资助项目(20902061)
关键词 非稳定型亚甲胺基叶立德 N-三甲基硅甲基苄胺 三组分1 3-偶极环加成 四氢吡咯 合成 unstabilized azomethine ylide N-（trimethylsilylmethyl） benzyl-amine three-component1,3-dipolar cycloaddition tetrahydropyrrol synthesis
分类号 O526.13 [理学—高压高温物理]
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参考文献14

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同被引文献17

  • 1Patti R S, Hireyuki O, Robert M W. Asymmetric,ste- reocontrollcd total synthesis of ( + ) and ( - )-spirot- ryprostatin B via a diastereoselective azomethine ylide [ 1,3 ] -dipolar cycloaddition reaction[ J ]. Tetrahedron, 2002,58:6311 - 6322.
  • 2Tony K, Yong L Z. Ring-selective synthesis of O-bet- erocycles from acyclic 3-O-allyl-monosaccharides via intramolecular nitrone-alkene cycloaddition [ J ]. Tetra- hedron ,2001,57 : 1573 - 1579.
  • 3James M, Bin W. Highly enantioselective Ag( I)-cata- lyzed [ 3 + 2 ] cycloaddition of azo-methine ylides [ J ]. J Am Chem Soc ,2002,124 : 13400 - 13401.
  • 4Ian S Y, Michael A K. Three-component homo 3 + 2 dipolar cycloaddition:A dlversity-oriemed synthesis of tetrahydro-1,2-oxazinas and FR900482 skeletal conge- ners[ J]. Organic Letters ,2004,6 : 139 - 141.
  • 5Williams R M, Zhai W, Aldous D J, et al. Asymmet- ric [ 1,3 ] -dipolar cyclo-addition reaction: Synthesis of highly substituted proline derivatives[J]. J Org Chore, 1992,57:6527 - 6532.
  • 6Hamper B C, Dukesherer D R, South M S. Solid- phase synthesis of proline analogs via a three compo- nent 1,3-dipolar cycloa-ddition [ J ]. Tetrabedron Let- tcrs, 1996,37:3671 - 3674.
  • 7Sebahar P R, Williams R M. The asymmetric total synthesis of ( + )- and ( -)-spiroo-tryprostatin B [J]. J Am Chem Soe,2000,122:5666-5667.
  • 8Ahrendt K A, Williams R M. A concise asymmetric synthesis of the ADE fragment of nakadomarin A [ J ]. Organic Letters,2004,6:4539 - 4541.
  • 9Wilson N S, Sarko C R, Roth G P. Microwave-assis- ted synthesis of a [ 3 + 2 ] cyclo-addition library [ J ]. Tetrahedron Lett ,2001,42:8939 - 8941.
  • 10Li G Y, Chen J, Yu W Y, et al. Stereo-selective synthesis of functionalized pyrrolidines by ruthenium porphyrin-catalyzed decomposition of ot-diazo esters and cascade azomethine ylide formation 1,3-dipolar cycloaddition reactions [ J ]. Organic Letters, 2003,5: 2153 - 2156.
合成化学
2012年 第4期

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