This book connects a retrosynthetic or disconnection approach with synthetic methods in the preparation of target molecules from simple, achiral ones to complex, chiral structures in the optically pure form. Retrosynthetic considerations and asymmetric syntheses are presented as closely related topics, often in the same chapter, underlining the importance of retrosynthetic consideration of target molecules neglecting stereochemistry and equipping readers to overcome the difficulties they may encounter in the planning and experimental implementation of asymmetric syntheses. This approach prepares students in advanced organic chemistry courses, and in particular young scientists working at academic and industrial laboratories, for independently solving synthetic problems and creating proposals for the synthesis of complex structures.

The application of biocatalysis in organic synthesis is rapidly gaining popularity amongst chemists. Compared to traditional synthetic methodologies biocatalysis offers a number of advantages in terms of enhanced selectivity (chemo-, regio-, stereo-), reduced environmental impact and lower cost of starting materials. Together these advantages can contribute to more sustainable manufacturing processes across a wide range of industries ranging from pharmaceuticals to biofuels. The biocatalytic toolbox has expanded significantly in the past five years and given the current rate of development of new engineered biocatalysts it is likely that the number of available biocatalysts will double in the next few years. This textbook gives a comprehensive overview of the current biocatalytic toolbox and also establishes new guidelines or rules for “biocatalytic retrosynthesis”. Retrosynthesis is a well known and commonly used technique whereby organic chemists start with the structure of their target molecule and generate potential starting materials and intermediates through a series of retrosynthetic disconnections. These disconnections are then used to devise a forward synthesis, in this case using biocatalytic transformations in some of the key steps. Target molecules are disconnected with consideration for applying biocatalysts, as well as chemical reagents and chemocatalysts, in the forward synthesis direction. Using this textbook, students will be able to place biocatalysis within the context of other synthetic transformations that they have learned earlier in their studies. This additional awareness of biocatalysis will equip students for the modern world of organic synthesis where biocatalysts play an increasingly important role. In addition to guidelines for identifying where biocatalysts can be applied in organic synthesis, this textbook also provides examples of current applications of biocatalysis using worked examples and case studies. Tutorials enable the reader to practice disconnecting target molecules to find the ‘hidden’ biocatalytic reactions which can be applied in the synthetic direction. The book contains a complete description of the current biocatalyst classes that are available for use and also suggests areas where new enzymes are likely to be developed in the next few years. This textbook is an essential resource for lecturers and students studying synthetic organic chemistry. It also serves as a handy reference for practicing chemists who wish to embed biocatalysis into their synthetic toolbox.

K.C. Nicolaou - Winner of the Nemitsas Prize 2014 in Chemistry This book is a must for every synthetic chemist. With didactic skill and clarity, K. C. Nicolaou and E. Sorensen present the most remarkable and ingenious total syntheses from outstanding synthetic organic chemists. To make the complex strategies more accessible, especially to the novice, each total synthesis is analyzed retrosynthetically. The authors then carefully explain each synthetic step and give hints on alternative methods and potential pitfalls. Numerous references to useful reviews and the original literature make this book an indispensable source of further information. Special emphasis is placed on the skillful use of graphics and schemes: Retrosynthetic analyses, reaction sequences, and stereochemically crucial steps are presented in boxed sections within the text. For easy reference, key intermediates are also shown in the margins. Graduate students and researchers alike will find this book a gold mine of useful information essential for their daily work. Every synthetic organic chemist will want to have a copy on his or her desk.

The world is chiral. Most of the molecules in it are chiral, and asymmetric synthesis is an important means by which enantiopure chiral molecules may be obtained for study and sale. Using examples from the literature of asymmetric synthesis (more than 1300 references), the aim of this book is to present a detailed analysis of the factors that govern stereoselectivity in organic reactions. It is important to note that the references were each individually checked by the authors to verify relevance to the topics under discussion. The study of stereoselectivity has evolved from issues of diastereoselectivity, through auxiliary-based methods for the synthesis of enantiomerically pure compounds (diastereoselectivity followed by separation and auxiliary cleavage), to asymmetric catalysis. In the latter instance, enantiomers (not diastereomers) are the products, and highly selective reactions and modern purification techniques allow preparation - in a single step - of chiral substances in 99% ee for many reaction types. After an explanation of the basic physical-organic principles of stereoselectivity, the authors provide a detailed, annotated glossary of stereochemical terms. A chapter on "Analytical Methods" provides a critical overview of the most common methods for analysis of stereoisomers. The authors then follow the 'tried-and-true' format of grouping the material by reaction type. Thus, there are four chapters on carbon-carbon bond forming reactions (enolate alkylations, organometal additions to carbonyls, aldol and Michael reactions, and cycloadditions and rearrangements), one chapter on reductions and hydroborations (carbon-hydrogen bond forming reactions), and one on oxidations (carbon-oxygen and carbon-nitrogen bond forming reactions). Leading references are provided to natural product synthesis that have been accomplished using a given reaction as a key step. In addition to tables of examples that show high selectivity, a transition state analysis is presented to explain - to the current level of understanding - the stereoselectivity of each reaction. In one case (Cram's rule) the evolution of the current theory is detailed from its first tentative (1952) postulate to the current Felkin-Anh-Heathcock formalism. For other reactions, only the currently accepted rationale is presented. Examination of these rationales also exposes the weaknesses of current theories, in that they cannot always explain the experimental observations. These shortcomings provide a challenge for future mechanistic investigations.

Asymmetric synthesis remains a challenge to practicing scientistsas the need for enantiomerically pure or enriched compoundscontinues to increase. Over the last decade, a large amount ofliterature has been published in this field. Principles andApplications of Asymmetric Synthesis consolidates and evaluates themost useful methodologies into a one-volume resource for theconvenience of practicing scientists and students. Authored by internationally renowned scientists in the field, thisreliable reference covers more than 450 reactions and includesimportant stoichiometric as well as catalytic asymmetric reactions.The first chapter reviews the basic principles, commonnomenclature, and analytical methods, and the remainder of the bookis organized according to reaction type. The text examines suchtopics as: Carbon-carbon bond formations involving carbonyls, enamines,imines, and enolates Asymmetric C-O bond formations including epoxidation,dihydroxylation, and aminohydroxylation Asymmetric synthesis using the Diels-Alder reaction and othercyclizations Applications to the total synthesis of natural products Use of enzymes in asymmetric synthesis Practicing chemists in the pharmaceutical, fine chemical, andagricultural professions as well as graduate students will findthat Principles and Applications of Asymmetric Synthesis affordscomprehensive and current coverage.

A first- and second-year undergraduate organic chemistry textbook, specifically geared to British and European courses and those offered in better schools in North America, this text emphasises throughout clarity and understanding.

The book is comprised of a series of exercises in synthetic organic chemistry based around recent published syntheses. The exercises are designed to provide challenges for people with varying levels of experience from final year students to academic staff and industrial group leaders, allowing them to increase their `vocabulary' of synthetic transformations. This novel approach, which actively involves the reader, would be an ideal source of topics for group discussions.