Asymmetric synthesis is an integral part of synthetic organic chemistry. Some of the reactions in this book were known prior to 1980, while several new ones, particularly catalytic asymmetric reactions, have been discovered in the recent years. The impact of this new class of reactions has been impressively extensive—both on organic and medicinal chemistry. These reactions have been accepted whole-heartedly by synthetic organic chemists in developing shorter routes for complex natural targets as well as in the manufacture of a wide range of drug intermediates.
Fundamentals of Asymmetric Synthesis has evolved from more than two decades of experience in teaching the subject. It deals with the fundamental concepts, terminology, mechanistic aspects and applications of asymmetric synthesis. It will be useful to teachers and students at the postgraduate level, open education learners, research scholars and researchers in all universities, institutions and industries.
Professor G L David Krupadanam obtained his Ph D from Osmania University in 1976. He has taught topics in synthetic and natural product organic chemistry at the postgraduate level for 33 years at the University College of Science, Osmania University. His 40 years of research experience has so far lead to 130 publications in SCI journals, two patents and four textbooks. He has guided 25 students in their research.
Krupadanam is the recipient of ‘The Best Teacher Award’ given by the Government of Andhra Pradesh and is a member of several professional, recruitment and regulatory bodies at the national level. At present, he is Advisor, Research & Development, Osmania University and a consultant to the pharma industry.
Introduction Terms, definitions and concepts in asymmetric synthesis Achiral and chiral molecules and their properties Prochirality Enantioselective and diastereoselective synthesis Methods for monitoring enantioselective and diastereoselective synthesis Methods for inducing asymmetry Chiral substrate controlled asymmetric reactions: Diastereoselection in acyclic systems Chiral auxiliary controlled asymmetric reactions—asymmetric α-alkylations Chiral stoichiometric reagent controlled asymmetric synthesis: Chiral boron reagents Chiral catalyst mediated asymmetric reactions: Enzymes Contents vii Chiral organometallic catalysed asymmetric reactions: Sharpless asymmetric epoxidations, dihydroxylations and aminohydroxylations Chiral organometallic catalysed asymmetric reactions Organocatalysts in asymmetric synthesis—chiral additive mediated reactions Asymmetric aldol reaction Asymmetric Diels–Alder reactions Stereoselective synthesis and stereospecific synthesis Annexure 1 Symmetry elements and symmetry operations Annexure 2 Point groups Annexure 3 Molecules with one chiral centre Annexure 4 Molecules with two or more chiral centres