By Spencer L. Seager, Michael R. Slabaugh
The 8th variation of the examine advisor and scholar recommendations handbook, up-to-date to mirror all adjustments to the middle textual content, checks scholars at the studying goals in each one bankruptcy and offers solutions to the entire even-numbered end-of-chapter workouts
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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.