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Chiral Amine Synthesis: Methods, Developments and Applications

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Chiral amines are powerful pharmacophores for defining new pharmaceutical drugs (Figure P.1) due to their high density of structural information and inherent ability for hydrogen bonding, yet their synthesis remains a challenge. That challenge is further appreciated when framed in the context of the following goal: the introduction of nitrogen into a commodity chemical or an advanced intermediate via an operationally simple procedure, preferably one step, with complete chemo , regio , diastereo , and enantiocontrol. Ten years ago this was an interesting goal to set and ponder, today it is within our grasp and the diversity of new and optimized methods developed since 2000 has enabled this sea change in technical capability. The book before you is therefore the first attempt to organize the results of this expanding field, by providing the overarching strategies that have elevated chiral amine synthesis from a specialized subtopic into the large field of diverse methods it now is. Perhaps unsurprisingly, the methods and concepts that have allowed this rise in stature are different from those in the field of chiral amino acid synthesis. The collected chapters that follow examine the vast majority of the relevant chiral amine literature (nonamino acids) from the years 2000 to 2009.

The key to assessing any methodology is substrate breadth; with this knowledge an immediate sense of substrate applicability, or lack thereof, is evident. From this vantage point a more restricted list of methods is chosen, with the final decision almost always driven by what is deemed as carrying higher priority: short timelines (number of reaction steps and overall yield of lower importance) or efficiency (number of reaction steps and overall yield of high importance). In general, the top methods can provide both, but this is not always the case and the chapter material has been carefully chosen to meet the demands of both types of research needs, namely, those of medicinal chemists and process research chemists. Aca demics will additionally enjoy the fact that each main chapter author has contributed three questions: one at the undergraduate level and two at the graduate level. Thus, this book could easily become a template for part of a graduate course.

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