Thiophosphoramide-Based Cooperative Catalysts for Bronsted Acid Promoted Ionic Diels-Alder Reactions
Thiophosphoramide-Based Cooperative Catalysts for Bronsted Acid Promoted Ionic Diels-Alder Reactions
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DOI：
10.1002/anie.201307133
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发表时间：
2013-12-09
影响因子：
16.6
通讯作者：
Nagorny, Pavel
中科院分区：
文献类型：
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作者：
Borovika, Alina;Tang, Pui-In;Nagorny, Pavel
除非另有说明，所有试剂均从商业供应商处购买，未经净化即可使用。甲苯(PhMe)、二氯甲烷(CH2Cl2)和乙醚(Et2O)在氮气气氛下通过活性氧化铝色谱柱(Innovative Technology PS-MD-5)过滤。所有的反应都是在氮气气氛下进行的，这些反应是在火焰干燥或烘干的玻璃器皿中通过磁力搅拌进行的。反应通过外部冷水浴冷却：冰水(0℃)、Neslab Cryotrol CB-80浸没冷却器(0~-60℃)或Neslab CryoCool浸没冷却器CC-100 II。反应混合物用SiliCycleSiliaFlash P60(230-400目)硅胶闪层析进行纯化。所有光谱记录在VARIAN VNMR700(700MHZ)、VARIAN VNMR500(500MHZ)、VARIAN MR400(400MHZ)、VARIAN INOVA500(500MHZ)光谱仪上，化学位移(δ)以百万分之几(Ppm)为单位报告，并根据IUPAC的建议参考内部四甲基硅烷的1H信号。1数据报告为(br=宽，S=单重态，d=双重态，t=三重态，q=四重态，qn=五重态，sext=六重态，m=多重态；耦合常数(S)，单位为赫兹；积分)。用美国密歇根大学质谱仪实验室的MICROMASS AutospecUltima或VG 70-250-S磁扇形质谱计记录高分辨质谱图。红外光谱在Perkin Elmer Spectrum BX FTIR光谱仪上以薄膜形式记录在氯化钠平板上。在波数(cm~(-1))处有吸收峰。所有商业上无法获得的缩醛和缩酮都是按照Lu和同事报告的步骤制备的。2个商业上无法获得的氢键供体是通过以前报道的方法合成的。3.
Unless otherwise stated, all reagents were purchased from commercial suppliers and used without purification. Toluene (PhMe), dichloromethane (CH2Cl2) and diethyl ether (Et2O) were filtered through a column (Innovative Technology PS-MD-5) of activated alumina under nitrogen atmosphere. All reactions were carried out under an atmosphere of nitrogen in flame-or oven-dried glassware with magnetic stirring. Reactions were cooled via external cooling baths: ice water (0 C), Neslab Cryotrol CB-80 immersion cooler (0 to-60 C) or Neslab Cryocool immersion cooler CC-100 II. Purification of the reactions mixtures was performed by flash chromatography using SiliCycleSiliaFlash P60 (230-400 mesh) silica gel. All spectra were recorded on Varian vnmrs 700 (700 MHz), Varian vnmrs 500 (500 MHz), Varian MR400 (400 MHz), Varian Inova 500 (500 MHz) spectrometers and chemical shifts (δ) are reported in parts per million (ppm) and referenced to the 1 H signal of the internal tetramethylsilane according to IUPAC recommendations. 1 Data are reported as (br= broad, s= singlet, d= doublet, t= triplet, q= quartet, qn= quintet, sext= sextet, m= multiplet; coupling constant (s) in Hz; integration). High resolution mass spectra (HRMS) were recorded on MicromassAutoSpecUltima or VG (Micromass) 70-250-S Magnetic sector mass spectrometers in the University of Michigan mass spectrometry laboratory. Infrared (IR) spectra were recorded as thin films on NaCl plates on a Perkin Elmer Spectrum BX FTIR spectrometer. Absorption peaks were reported in wavenumbers (cm-1). All commercially unavailable acetals and ketals were prepared following the procedure reported by Lu and coworkers. 2 Commercially unavailable hydrogen bond donors were synthesized by previously reported procedures. 3