手性合成要点绪论.ppt

Principles and Applications of Asymmetric Synthesis CHAPTER 1 Introduction The universe is dissymmetrical; for if the whole of the bodies which compose the solar system were placed before a glass moving with their individual movements,the image in the glass could not be superimposed on reality. . . . Life is dominated by dissymmetrical actions. I can foresee that all living species are primordially, in their structure, in their external forms, functions of cosmic dissymmetry. DLouis Pasteur Brief history 1801, Hauèy :quartz crystals exhibited hemihedral phenomena; 1809, Malus,:quartz crystals could induce the polarization of light; 1812, Biot:Right and left forms of quartz crystals rotated the plane of the polarized light in in different directions. 1815. Biot: differences between the rotation caused by quartz crystals and that caused by the solutions of organic compounds 1822, John Herschel: there was a correlation between hemihedralism and optical rotation. 1846-1848, Pasteur:the rotation of polarized light caused by different tartaric acid salt crystals was the property of chiral molecules. 1874. independent publications by J. H. vant Hoff and J. A. Le Bel dated the actual birth of stereochemistry 1.1 THE SIGNIFICANCE OF CHIRALITY AND STEREOISOMEIC DISCRIMINATION An object is chiral if it cannot be superimposed on its mirrorimage. In such a case, there are two possible forms of the same object, which are called enantiomers, and thus these two forms are said to be enantiomeric with each other. Enantiomers: have identical chemical and physical pro