Determination of the absolute stereochemistry of chiral biphenanthiryls in solution phase using chiroptical spectroscopic methods: 2,2 '-diphenyl-[3,3 '-biphenanthrene]-4,4 '-diol

Petrovic AG; Vick SE; Polavarapu PL

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Determination of the absolute stereochemistry of chiral biphenanthiryls in solution phase using chiroptical spectroscopic methods: 2,2 '-diphenyl-[3,3 '-biphenanthrene]-4,4 '-diol

机译：使用手性光谱法测定溶液相中手性联菲的绝对立体化学：2,2'-联苯-[3,3'-联菲] -4,4'-二醇

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Although the exciton coupling model has been widely used in the literature to suggest the absolute configuration using electronic circular dichroism (ECD) spectra, chiral biphenanthryl systems are one group of molecules where the application of the exciton model yields ambiguous conclusions. The use of 2,2'-diphenyl-[3,3'-biphenanthrene]-4,4'-diol, known as VAPOL, as a chiral ligand for enantioselective catalysis necessitates the reliable determination of its absolute configuration. Based on the X-ray diffraction data of its phosphoric amide derivative, the configuration of VAPOL has been determined in the literature to be (+)-(aS). The experimental vibrational circular dichroism, ECD and optical rotatory dispersion spectra, and corresponding quantum mechanical predictions of VAPOL are used in this manuscript to independently determine its absolute configuration.

机译：尽管激子耦合模型已在文献中广泛使用，以提出使用电子圆二色性（ECD）光谱的绝对构型，但手性联菲基系统是其中激子模型的应用得出模糊结论的一组分子。使用2,2'-二苯基-[3,3'-联菲] -4,4'-二醇（称为VAPOL）作为手性配体进行对映选择性催化，需要可靠地确定其绝对构型。基于其磷酸酰胺衍生物的X射线衍射数据，在文献中已将VAPOL的构型确定为（+）-（aS）。该手稿采用实验振动圆二色性，ECD和旋光色散谱以及相应的VAPOL量子力学预测来独立确定其绝对构型。

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《Chirality: The pharmacological, biological, and chemical consequences of molecular asymmetry》 |2008年第4期|共10页
作者
Petrovic AG; Vick SE; Polavarapu PL;
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正文语种 eng
中图分类分子生物学;
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VAPOL; absolute configuration; vibrational circular dichroism; electronic circular dichroism; optical rotation; vibrational spectra; density functional predictions; DENSITY-FUNCTIONAL THEORY; ELECTRONIC CIRCULAR-DICHROISM; CATALYTIC ASYMMETRIC AZIRIDINATION; AB-INITIO CALCULATION; VIBRATIONAL ASSIGNMENT; INFRARED-SPECTRA; VAPOL; PHENANTHRENE; CONFIGURATION; MOLECULES;

机译：VAPOL;绝对构型;振动圆二色性;电子圆二色性;旋光度;振动光谱;密度泛函预测;密度泛函理论;电子圆二色性;催化不对称叠氮化;AB初始计算;分度;振动;菲;构型;分子;

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1. Determination of the absolute stereochemistry of chiral biphenanthiryls in solution phase using chiroptical spectroscopic methods: 2,2 '-diphenyl-[3,3 '-biphenanthrene]-4,4 '-diol [J] . Petrovic AG, Vick SE, Polavarapu PL Chirality: The pharmacological, biological, and chemical consequences of molecular asymmetry . 2008,第3a4期

机译：使用手性光谱法测定溶液相中手性联菲的绝对立体化学：2,2'-联苯-[3,3'-联菲] -4,4'-二醇
2. Chemistry of Unique Chiral Olefins. 1. Synthesis, Enantioresolution, Circular Dichroism, and Theoretical Determination of the Absolute Stereochemistry of trans- and cis-1,1',2,2',3,3',4,4'-Octahydro-4,4'-biphenanthrylidenes [J] . Nobuyuki Harada, Akira Saito, Nagatoshi Koumura Journal of the American Chemical Society . 1997,第31期

机译：独特的手性烯烃化学。 1.合成，对映拆分，圆二色性和反式和顺式-1,1'，2,2'，3,3'，4,4'-八氢-4,4'-双菲蒽的绝对立体化学的理论测定
3. Photochemistry and absolute stereochemistry of unique chiral olefins, trans- and cis-1,1 ',2,2 ',3,3 ',4,4 '-octahydro-3,3 '-dimethyl-4,4 '-biphenanthrylidene [J] . Koumura N., Harada N. Chemistry Letters . 1998,第11期

机译：独特的手性烯烃，反式和顺式1,1'，2,2'，3,3'，4,4'-八氢-3,3'-二甲基-4,4'-联菲基亚萘基的光化学和绝对立体化学
4. Radiolysis of 2,2',3,3',4,4',5,5',6,6'-bromdiphenyl ether solutions by UV and electron beams [C] . Wenyan Shi, Jianzhong Gu, Wenjing Wu, International Conference on Energy, Environment and Sustainable Development . 2012

机译：通过UV和电子束辐射2,2'，3,3'，4,4'，5,6'，6,6'-溴二苯醚溶液
5. STUDIES IN STEREOCHEMISTRY. PART I: SYNTHESIS, RESOLUTION AND ABSOLUTE CONFIGURATION OF (E)-2,4-DIMETHYL-2-HEXENOIC ACID. PART II: THE DETERMINATION OF THE HEAT OF HYDROGENATION AND REARRANGEMENT BEHAVIOR OF 1,1'-SPIROBIINDENE. PART III: SYNTHESIS AND CHIROPTICAL PROPERTIES OF 5,7-DIOXOBICYCLO(2.2.2)OCT-2-ENE AND BICYCLO(2.2.2)OCTAN-2,5-DIONE. [D] . MORTON, GERALD HUNT. 1980

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6. Aplisulfamines New Sulfoxide-Containing Metabolites from an Aplidium Tunicate: Absolute Stereochemistry at Chiral Sulfur and Carbon Atoms Assigned Through an Original Combination of Spectroscopic and Computational Methods [O] . Anna Aiello, Ernesto Fattorusso, Concetta Imperatore, 2012

机译：Aplisulfamines来自Tun衣的新的含亚砜的代谢物：通过光谱学和计算方法的原始结合指定的手性硫和碳原子的绝对立体化学
7. Chemistry of Unique Chiral Olefins. 1. Synthesis, Enantioresolution, Circular Dichroism, and Theoretical Determination of the Absolute Stereochemistry of trans- and cis-1,1´,2,2´,3,3´,4,4´-Octahydro-4,4´-biphenanthrylidenes [O] . Harada Nobuyuki, Saito Akira, Koumura Nagatoshi, 1997

机译：独特的手性烯烃化学。 1.合成，对映拆分，圆二色性和反式和顺式1,1´，2,2´，3,3´，4,4´-八氢-4,4´-联菲基的绝对立体化学的理论确定

Determination of the absolute stereochemistry of chiral biphenanthiryls in solution phase using chiroptical spectroscopic methods: 2,2 '-diphenyl-[3,3 '-biphenanthrene]-4,4 '-diol

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