Amino acid fluorides: viable tools for synthesis of peptides, peptidomimetics and enantiopure heterocycles

Prabhu, Girish; Narendra, N.; Basavaprabhu,; Panduranga, Veladi; Sureshbabu, Vommina V.

doi:10.1039/c4ra16142d

Cited by 48 publications

(28 citation statements)

References 190 publications

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“…[1] Most carboxylic acid derivatives,such as acids,acylhalides,anhydrides,esters,and amides,h ave been successfully used as electrophilic partners in cross-coupling reactions. [1] Most carboxylic acid derivatives,such as acids,acylhalides,anhydrides,esters,and amides,h ave been successfully used as electrophilic partners in cross-coupling reactions.…”

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confidence: 99%

Acid Fluorides in Transition‐Metal Catalysis: A Good Balance between Stability and Reactivity

Blanchard

Bizet

2019

Angew Chem Int Ed

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Dedicated to Dr.Philippe Bisseret on the occasion of his retirement acid fluorides ·C À Ffunctionalization ·cross-coupling · decarbonylation ·transition-metal catalysis Abstract: Several recent reports outlined the singular reactivity of acid fluorides as excellent electrophiles in transition-metal catalysis.These species undergo oxidative addition of the metal into the CÀFbond;then, retention or release of the CO moiety can occur and be controlled by tuning the catalytic system and the reaction parameters.A cid fluorides,w hichc an be derived from carboxylic acids,s how good stability and high reactivity in aw ide range of possible functionalizations with nucleophiles.T heir use provides an interesting alternative to that of the parent carboxylic acid derivatives (acid chlorides,e sters, amides,acids,o raldehydes).

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confidence: 99%

Acid Fluorides in Transition‐Metal Catalysis: A Good Balance between Stability and Reactivity

Blanchard

Bizet

2019

Angew Chem Int Ed

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“…[1] Acyl fluorides, the stable and readily accessible carboxylic acid derivatives, are traditionally used as acylation reagents via nucleophilic substitution or transition-metal (TM) catalyzed cross-coupling reaction. [2] Recently, TM-catalyzed decarbonylative reactions of aroyl fluorides have been successfully realized for a number of transformations, including trifluoromethylation, [3] Suzuki-Miyaura type arylation, [4] reduction, [5] alkylation [6] and direct CÀ H arylation [7] (Scheme 1a). In addition, a few, although rare, cases of carbon-heteroatom bond formation with acyl fluorides as arylation precursors were also reported, including the Ni-catalyzed borylation [8] and silylation [9] of acyl fluorides.…”

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confidence: 99%

Synthesis of Arylstannanes via Palladium‐Catalyzed Decarbonylative Coupling of Aroyl Fluorides

et al. 2019

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Aryl stannanes are valuable precursors in organic transformations, but their synthetic methods are limited. Here we present a Pd‐catalyzed decarbonylative stannylation of acid fluorides in the absence of exogenous base. Various aryl stannanes were efficiently prepared from bench‐stable transition metal catalyst and ligand with broad functional group compatibility and substrate scope including natural products and pharmaceuticals. This protocol was also successfully used to a late‐stage diversification of an existing uricosuric drug probenecid.

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“…However, researchers have struggled to develop approaches to achieve such scaffolds . Owing to their optical purity, synthetically transformable structure/functionality and chiral centres, AAs have also become an important tool for asymmetric synthesis and chiral catalysis …”

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confidence: 99%

Synthesis of Disubstituted Pyrazino‐Oxazine Derivatives with Controlled Stereochemistry

2017

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Herein, we report a simple synthesis of disubstituted pyrazino‐oxazines with controlled stereochemistry using readily available building blocks: N‐Fmoc‐protected α‐amino acids and 2‐bromo ketones. The convenient solid‐phase synthesis afforded polymer‐supported derivatives of N‐alkylated N‐acylated tert‐butylserine, which were subjected to spontaneous cyclative cleavage to yield the corresponding pyrazine intermediates. The target 1,7,8,9a‐tetrahydropyrazino[2,1‐c][1,4]oxazine‐6,9‐diones were obtained in two steps by acid‐mediated cleavage of the tert‐butyl group followed by cyclization of the oxazine scaffold.

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Amino acid fluorides: viable tools for synthesis of peptides, peptidomimetics and enantiopure heterocycles

Abstract: This review provides a broad perspective of the uses of amino acid fluorides in the synthesis of peptides and a wide range of other molecules including peptidomimetics, heterocycles and biologically active molecules.

Cited by 48 publications

References 190 publications

Acid Fluorides in Transition‐Metal Catalysis: A Good Balance between Stability and Reactivity

Acid Fluorides in Transition‐Metal Catalysis: A Good Balance between Stability and Reactivity

Synthesis of Arylstannanes via Palladium‐Catalyzed Decarbonylative Coupling of Aroyl Fluorides

Synthesis of Disubstituted Pyrazino‐Oxazine Derivatives with Controlled Stereochemistry

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