Design of Peptidyl Thiourea Derivatives as Organocatalysts for the Asymmetric Ring Opening of <i>meso</i>‐Stilbene Oxides

Chimni, Swapandeep Singh; Kumar, Vijay; Bala, Neeraj

doi:10.1002/ajoc.201402040

Cited by 12 publications

(10 citation statements)

References 75 publications

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“…In 2014, Chimni and coworkers reported a peptide catalyzed, asymmetric ring-opening reaction of meso-stilbene oxides 5.28 with N-phenylpiperazine 5.29 to access chiral amino alcohols 5.30 (Figure 94). 233 The general catalyst design centered on short, β-turn forming sequences capped with an N-terminal thiourea moiety. In that way, the authors intended to capitalize on the demonstrated ability of thioureas to activate electrophiles through H-bonding interactions, 234 as well as the folded secondary structures of peptides to provide a robust chiral environment for asymmetric induction.…”

Section: Meso-epoxide Openingmentioning

confidence: 99%

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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Section: Meso-epoxide Openingmentioning

confidence: 99%

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

et al. 2020

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“…[24] In 2014, Chimni and co-authors designed ac hiral combined thiourea peptidyl scaffold for the desymmetrization of mesoepoxides with amines. [28] The idea wast oe xploit ad ual activation of the epoxide,p rovided by the thiourea group and the nucleophile by ag eneric site in the chiral peptidyl moiety.A ccording to the literature, [29] ap eptide linker incorporating bturn conformations, introduced with l-Pro-d-Pro and d-Pro-Gly dipeptides, would have been expected to be the most effective. After apreliminary screening of peptidyl thiourea catalysts and reactionc onditions on model reaction of cis-stilbene oxide and N-phenyl piperazine, catalyst 9a,u sed at 10 mol %l oading, was selected to explore the scope of the ARO reaction in CH 3 CN as solventatr oom temperature (Scheme 4).…”

Section: Intramolecular B-elimination To Allylicalcoholsmentioning

confidence: 99%

“…In 2014, Chimni and co‐authors designed a chiral combined thiourea peptidyl scaffold for the desymmetrization of meso ‐epoxides with amines . The idea was to exploit a dual activation of the epoxide, provided by the thiourea group and the nucleophile by a generic site in the chiral peptidyl moiety.…”

Section: Desymmetrization Of Meso‐epoxidesmentioning

confidence: 99%

Organocatalytic Asymmetric Reactions of Epoxides: Recent Progress

Meninno

Lattanzi

2016

Chemistry A European J

115

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In this Minireview recent advances in the asymmetric reactions of meso and racemic epoxides promoted by organocatalysts is reviewed. Organic promoters, such as chiral phosphoric acids, amino- and peptidyl thioureas, and sulfinamides, have been successfully used for a variety of enantioselective transformations of epoxides under catalytic conditions, involving direct nucleophilic attack at the oxirane ring, base-catalysed β-eliminations and Brønsted acid catalysed 1,2-rearrangements. Accordingly, highly valuable enantioenriched 1,2-functionalised alcohols, carbonyl compounds and nitroepoxides are attainable. Dual activation of the reagents, provided by the organocatalysts, appears to be the most recurrent strategy, potentially suitable to face other unmet challenges in asymmetric ring-opening reactions of epoxides.

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“…We choose L‐Pro‐D‐Pro template to introduce a turn in the peptide chain, since in addition to the ease of LD and DL turn formation, it makes the peptide chain to adopt type II or type‐II′ β ‐turn. This peptidyl thiourea XIX was then used to catalyze the asymmetric ring opening of cis ‐stilbene oxides 58 with N ‐phenylpiperazines 59 . The desired chiral β ‐amino alcohols 60 were obtained in 81–89 % yield with up to 95 % ee after recrystallization.…”

Section: Introductionmentioning

confidence: 99%

Journey Heading towards Enantioselective Synthesis Assisted by Organocatalysis

Kaur

Chauhan

Singh

et al. 2017

The Chemical Record

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This personal account summarizes the design of various organocatalysts derived from amino acids and Cinchona alkaloids and their applications in enantioselective carbon-carbon and carbon-nitrogen bond formation reactions. This account begins with the short description of the background of asymmetric organocatalysis. Various types of reactions like aldol reaction, Michael reaction, aza-Henry reaction, Morita-Baylis-Hillman reaction are described in this account.

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Design of Peptidyl Thiourea Derivatives as Organocatalysts for the Asymmetric Ring Opening of meso‐Stilbene Oxides

Cited by 12 publications

References 75 publications

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

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

Organocatalytic Asymmetric Reactions of Epoxides: Recent Progress

Journey Heading towards Enantioselective Synthesis Assisted by Organocatalysis

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