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The enantioselective nucleophilic addition of prochiral C¼O and C¼N moieties to the corresponding saturated chiral products is one of the most important stereoselective transformations on both the laboratory and the industrial scale. Although, over the past few decades, remarkable scientific achievements have been made in these research areas by using a variety of transitional metal-based catalysts, the sensitivity of the reaction to moisture and oxygen, as well as the toxic metal contamination of the product, usually restrict its practical application. Thus, currently, there is much interest in chiral organocatalysts, as they tend to be less toxic and more environmental friendly than traditional metal-based catalysts [1]. They are usually robust and thus tolerate moisture and oxygen, so that they usually do not demand any special reaction conditions.The naturally occurring cinchona alkaloids (Figure 8.1), as described in other chapters of this book, have proven to be powerful organocatalysts in most major chemical reactions. They possess diverse chiral skeletons and are easily tunable for diverse catalytic reactions through different mechanisms, which make them privileged organocatalysts. The vast synthetic potential of cinchona alkaloids and their derivatives in the asymmetric nucleophilic addition of prochiral C¼O and C¼N bonds has also been well demonstrated over the last decade.In this chapter, the current state of the art on the applications of cinchona alkaloids and their derivatives as chiral catalysts in the enantioselective nucleophilic addition of prochiral C¼O and C¼N bonds is discussed. The schemes exemplified in this chapter demonstrate the indispensable role of cinchona alkaloids as catalysts in these important research areas.
The enantioselective nucleophilic addition of prochiral C¼O and C¼N moieties to the corresponding saturated chiral products is one of the most important stereoselective transformations on both the laboratory and the industrial scale. Although, over the past few decades, remarkable scientific achievements have been made in these research areas by using a variety of transitional metal-based catalysts, the sensitivity of the reaction to moisture and oxygen, as well as the toxic metal contamination of the product, usually restrict its practical application. Thus, currently, there is much interest in chiral organocatalysts, as they tend to be less toxic and more environmental friendly than traditional metal-based catalysts [1]. They are usually robust and thus tolerate moisture and oxygen, so that they usually do not demand any special reaction conditions.The naturally occurring cinchona alkaloids (Figure 8.1), as described in other chapters of this book, have proven to be powerful organocatalysts in most major chemical reactions. They possess diverse chiral skeletons and are easily tunable for diverse catalytic reactions through different mechanisms, which make them privileged organocatalysts. The vast synthetic potential of cinchona alkaloids and their derivatives in the asymmetric nucleophilic addition of prochiral C¼O and C¼N bonds has also been well demonstrated over the last decade.In this chapter, the current state of the art on the applications of cinchona alkaloids and their derivatives as chiral catalysts in the enantioselective nucleophilic addition of prochiral C¼O and C¼N bonds is discussed. The schemes exemplified in this chapter demonstrate the indispensable role of cinchona alkaloids as catalysts in these important research areas.
The manipulation of the transition states of a chemical process is essential to achieve the desired selectivity. In particular, transition states of chemical reactions can be significantly modified in a confined environment. We report a catalytic reaction with remarkable amplification of stereochemical information in a confined water cage. Surprisingly, this amplification is significantly dependent on droplet size. This water-induced chirality amplification stems from the hydrophobic hydration effects, which ensures high proximity of the catalyst and substrates presumably at the transition state, leading to higher enantioselectivity. Flow and batch reactors were evaluated to confirm the generality of this water-induced chirality amplification. Our observation on efficient chiral induction in confined water cages might lead to an understanding of the chirality amplification in the prebiotic era, which is a key feature for the chemical evolution of homochirality.
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