By Peter I. Dalko
A much-needed assessment reflecting the advancements over the last 5 years, this is often the main entire guide on organocatalysis. As such, all appropriate catalyst platforms are mentioned intimately, in addition to key concepts, response kinds, and critical purposes in overall synthesis. the 1st volumes conceal catalyst buildings and fundamental activation kinds. those chapters permit readers to familiarize themselves with the really advanced interactions that make organocatalytic reactions selective; to achieve an perception into the best catalyst varieties; and to appreciate the significance of actual parameters that effect reactivity and selectivity. quantity 3 is dependent round response forms, i.e. nucleophile additions to C=X and C=C bonds; Friedel-Crafts reactions, organocatalytic sigmatropic reactions, regioselective reactions and desymmetrization thoughts, ring-forming reactions, multicomponent (domino) reactions, multicatalyst platforms and the appliance of organocatalytic reactions in multistep synthesis are mentioned. An appendix recollecting catalyst constructions with the enough cross-references to the corresponding chapters rounds off the book.
With its contributions written through pioneers of the organocatalysis box, this ebook presents non-specialists with an creation to the subject in addition to serving as a important resource for researchers in academia and looking for an up to date and entire evaluate of this promising region of man-made natural chemistry
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Extra info for Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications
8 1 Proline-Related Secondary Amine Catalysts and Applications CHO + Ar O cat 17-type (20 mol%) BnNH2 R mol. 4 While some examples of prolinamide-catalyzed enantioselective Biginelli condensation [104, 105] and other types of C–C bond formation [106, 107] are known, their synthetic utility is unclear. Finally, for convenience, with regard to asymmetric heteroatom functionalization and transfer hydrogenation using prolinamides as catalysts, only references are given [108–114]. 3 Prolinamine and Related Catalysts Among several organocatalysts derived from L-proline (1) as a chiral source, pyrrolidine–tertiary amine conjugates constitute a powerful and useful family in asymmetric synthesis .
Furthermore, different types of catalysts such as 29 have been shown to be useful in asymmetric Michael addition reactions [145–148]. While catalyst 22/23 has been known to be valuable in other C–C bond-forming strategies, for example, 1,3-dipolar cycloaddition , hetero-Diels–Alder reaction , Friedel–Crafts-type alkylation , double-Michael reaction , [2,3]Wittig rearrangement , and Claisen–Schmidt condensation , only references are given here. 7) , have also been reported, they have been demonstrated in only a limited number of experiments.
In this field, the chirality of a pyrrolidine fragment plays a critical role, and the principal concept that underlies the development of new catalysts can be simply explained as the attachment of acidic sites in place of a carboxylic acid group to the side chain. Accordingly, several catalysts with various acidic functionalities have been developed . 1). 2 . A subtle change in the side-chain assembly may change the pKa value in the range 8–20, which would have a significant effect on the strength of hydrogen bonding, and thus the catalytic activity and selectivity may be affected.