ChemInform Abstract: Catalytic, Asymmetric Halofunctionalization of Alkenes — A Critical Perspective

Denmark, Scott E.; Kuester, William; Burk, Matthew T.

doi:10.1002/chin.201310227

Cited by 1 publication

(3 citation statements)

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“…A wide variety of asymmetric halogenation methodologies have been developed over the past three decades, ranging from α-halogenations of carbonyl compounds 409,410 and olefin halofunctionalizations 411,412 to dihalogenation reactions of allylic alcohols. 413 In recent years, the application of peptide-based catalysts in this area has led to a significant expansion of scope and mechanistic understanding.…”

Section: Halogenationmentioning

confidence: 99%

“…These reactions typically proceed through the formation of a bridged haliranium ion followed by trapping with nucleophiles, allowing for the 1,2difunctionalization of the olefin starting material. 411,412,425 In many cases, formation of the haliranium ion intermediate renders these reactions stereospecific, making them quite valuable in organic synthesis. Olefin halolactonization, in particular, has found wide use as a reliable approach for the formation of lactone products that can be subsequently derivatized via displacement of the adjacent halide.…”

Section: Asymmetric Bromolactonizationmentioning

confidence: 99%

“…451 However, catalytic asymmetric variants have been difficult to realize through the years. 411 This is due, in part, to the challenge associated with olefin-to-olefin haliranium ion transfer, which ultimately leads to product racemization if the rate is competitive with that of nucleophilic addition. In this context, Borhan and coworkers became interested in developing asymmetric halolactonization methods.…”

Section: Asymmetric Bromolactonizationmentioning

confidence: 99%

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Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms

et al. 2020

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Low molecular weight synthetic peptides have been demonstrated to be effective catalysts for an increasingly wide array of asymmetric transformations. In many cases, these peptide-based catalysts have enabled novel multifunctional substrate activation modes and unprecedented selectivity manifolds. These features, along with their ease of preparation, modular and tunable structures, and often biomimetic attributes make peptides well-suited as chiral catalysts, and of broad interest. Many examples of peptide-catalyzed asymmetric reactions have appeared in the literature since the last survey of this broad field in Chemical Reviews (Chem. Rev. 2007, 107, 5759-5812). The overarching goal of this new review is to provide a comprehensive account of the numerous advances in the field. As a corollary to this goal, we survey the many different types of catalytic reactions, ranging from acylation to C-C bond formation, in which peptides been successfully employed. In so doing, we devote significant discussion to the structural and mechanistic aspects of these reactions that are perhaps specific to peptide-based catalysts and their interactions with substrates and/or reagents.

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