Chemistry for today. Study guide and student solutions by Spencer L. Seager, Michael R. Slabaugh PDF

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 [115].

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 [149], hetero-Diels–Alder reaction [150], Friedel–Crafts-type alkylation [151], double-Michael reaction [152], [2,3]Wittig rearrangement [153], and Claisen–Schmidt condensation [154], only references are given here. 7) [157], 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]. 1). 2 [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.

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