Chapter 7 — Further Reading

On chirality and stereochemistry

• Eliel, E. L., and Wilen, S. H. (1994). Stereochemistry of Organic Compounds. Wiley. 1,200 pages; the authoritative reference.
• Clayden, Greeves, Warren. (2012). Organic Chemistry, 2nd edition. Chapters 14-16 on stereochemistry.
• Morris, D. G. (2001). Stereochemistry. Royal Society of Chemistry. Short and accessible.

On biological chirality

• Brunken, W. (ed.) (2007). Chirality in Drug Research. Wiley-VCH.
• McConathy, J., and Owens, M. J. (2003). Stereochemistry in drug action. Primary Care Companion to the Journal of Clinical Psychiatry, 5(2), 70–73.
• Leffingwell, J. C. (2003). Chirality and bioactivity. Leffingwell Reports, 3(1), 1–27.

On asymmetric synthesis (Chapter 7 Case Study 2)

• Knowles, W. S. (2002). Asymmetric hydrogenations (Nobel Lecture). Angewandte Chemie International Edition, 41, 1998–2007.
• Noyori, R. (2002). Asymmetric catalysis (Nobel Lecture). Angewandte Chemie International Edition, 41, 2008–2022.
• Sharpless, K. B. (2002). Searching for new reactivity (Nobel Lecture). Angewandte Chemie International Edition, 41, 2024–2032.
• Ojima, I. (ed.) (2010). Catalytic Asymmetric Synthesis, 3rd edition. Wiley.

Online tools

• Sigma-Aldrich chirality resources — sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/organic-reaction-toolbox/chiral-switches
• IUPAC Nomenclature for stereoisomers: official rules for R/S, E/Z, D/L, cis/trans naming.

Suggested practice

Take ten drug structures from PubChem. For each: 1. Find the stereocenters. 2. Assign R/S (using Cahn-Ingold-Prelog priorities). 3. Look up which enantiomer is the active form. 4. Note whether the drug is marketed as a single enantiomer or a racemate.

An hour of this exercise builds the R/S assignment skill that is the most-often-failed part of many organic chemistry exams.