Adopting a novel approach to the topic by combining theoretical knowledge and practical results, this book presents the most popular and useful computational and experimental methods applied for studying the stereochemistry of chemical reactions and compounds. The text is clearly divided into three sections on fundamentals, spectroscopic and computational techniques, and applications in organic synthesis. The first part provides a brief introduction to the field of chirality and stereochemistry, while the second part covers the different methodologies, such as optical rotation, electronic circular dichroism, vibrational circular dicroism, and Raman spectroscopy. The third section then goes on to describe selective examples in organic synthesis, classified by reaction type, i.e. enantioselective, chemoselective and stereoselective reactions. A final chapter on total synthesis of natural products rounds off the book. A valuable reference for researchers in academia and industry working in the field of organic synthesis, computational chemistry, spectroscopy or medicinal chemistry.
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A simple chiral molecule just contains one sp3-hybridized carbon that connects four different groups, such as chiral molecule 1 (
, Figure 1.1). Its mirror image structure, namely the enantiomer, is 2, which has the same relative configuration (RC) but different absolute configuration (AC); for example, when
, chiral molecule 1 has (R)-AC and 2 has (S)-AC. Both have the same chemical characteristics, such as the transition state (TS) barrier (reaction activation energy) in reactions in the absence of a chiral catalyst or a chiral auxiliary compound, and physical characteristics such as melting and boiling point and magnetic shielding constant for each corresponding atom. However, in a beam of circularly polarized light (CPL), the enantiomers exhibit opposite characteristics. For example, both have the same absolute optical rotation (OR) values, but their OR signs are reversed. The different optical characteristics are the basis allowing us to identify their AC.
Figure 1.1 Enantiomers and polarized light.
As a widely known phenomenon, chirality, also named as handedness, brings out many mysteries that we have not known until now. For example, the l-amino acids were selected in peptide formation for the origin of life instead of d-amino acids. d-sugars were used instead of l-sugars. That is the amazing natural choice. Although we do not know why Nature selected different chiral molecules in life, it does not affect us in the study of the handedness of molecules and other materials.
Absolutely, because of the natural selection of l-amino acids and d-sugars in life formation, different chiral compounds must, logically, have different effects on the life process. Historically, a mixture of the (R) and (S) enantiomers (3 and 4) was used as a medicine for preventing vomiting in pregnant women in European countries – but not in America – in the 1960s. Many infants with deformed limbs were born. This was caused by a chiral chemical compound, (S)-thalidomide (4), which can be isomerized from (R)-3 (Scheme 1.1) [1a–c]. In America, this tragic issue was avoided because Frances O. Kelsey in the Food and Drug Administration (FDA) could not find evidences from the documents handed by the pharmaceutical company to confirm that it was not harmless to the central nervous system. This doubt delayed the approval of this medicine for use in the United States, and just because of this action it saved many infants and families in the United States.
Scheme 1.1 Isomerization of (R)-thalidomide to its (S)-enantiomer [1].
Tertodotoxin (5) is a strong toxic chiral compound that is isolated from globefish [1d]. The strong toxicity comes from the (S) AC of C9. Once C9 becomes (R) AC, its severe toxicity almost disappears.
More examples can be found with different bioactivities. Some pairs of enantiome...
