Twisted Amide Analogues of Tröger’s Base

Artacho, Josep; Ascic, Erhad; Rantanen, Toni; Karlsson, J. Olle; Wallentin, Carl‐Johan; Wang, Ruiyao; Wendt, Ola F.; Harmata, Michael; Snieckus, Victor; Wärnmark, Kenneth

doi:10.1002/chem.201103228

Cited by 34 publications

(35 citation statements)

References 78 publications

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“…315 A complete hydrolysis was observed in a 0.58 N solution of HCl within 400 min, while kinetic and 18 O labeling studies suggested irreversible collapse of the protonated tetrahedral intermediate. 315 …”

Section: Reactivity Of Bridged Lactams and Related Heterocyclesmentioning

confidence: 95%

Chemistry of Bridged Lactams and Related Heterocycles

2013

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CONTENTS 1. Introduction 5702 2. General Properties of Bridged Lactams 5703 2.1. Distortion Parameters of Bridged Lactams 5703 2.2. Bond Lengths of Bridged Lactams 5703 2.3. Spectroscopic Properties of Bridged Lactams 5703 2.4. Analogy of Bridged Lactams to Bridgehead Olefins 5704 2.5. Chemical and Biological Significance of Distorted Amides 5704 3. Synthesis of Historically Important Bridged Lactams 5704 3.1. Quinuclidone Derivatives 5704 3.2. Adamantanone Derivatives 5707 4. Synthesis of Bridged Lactams with the N−(CO) Bond on a Two-Carbon or Larger Bridge, ([m. (≥2).n] Type) 5708 4.1. Condensation Reactions Forming the N− C(O) Bond 5708 4.2. Heck Reactions 5711 4.3. Diels−Alder Reactions 5712 4.4. Carbene Insertion Reactions 5713 4.5. Reactions via Radical Intermediates 5714 4.6. Miscellaneous Examples 5714 5. Synthesis of Bridged Lactams with the N−(CO) Bond on a One-Carbon Bridge, ([m.1.n] Type) 5715 5.1. Carbene Insertion Reactions 5715 5.2. Schmidt Reactions 5716 5.3.

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Section: Reactivity Of Bridged Lactams and Related Heterocyclesmentioning

confidence: 95%

Chemistry of Bridged Lactams and Related Heterocycles

2013

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“…[21,22] Initially, mono-twisted amide was formed by formylation and air-induced oxidation/decarboxylation. [21,22] Initially, mono-twisted amide was formed by formylation and air-induced oxidation/decarboxylation.…”

Section: Trçger's Base Twistedamidesmentioning

confidence: 99%

“…In 2012, Harmata, Snieckus, and Wärnmark reported new Tröger's base twisted amides by oxidation at the benzylic position as potential scaffolds for molecular recognition (Scheme A) . Initially, mono‐twisted amide was formed by formylation and air‐induced oxidation/decarboxylation.…”

Section: Twisted Amides: New Frontiersmentioning

confidence: 99%

Twisted Amides: From Obscurity to Broadly Useful Transition‐Metal‐Catalyzed Reactions by N−C Amide Bond Activation

Liu

Szostak

2017

Chemistry A European J

291

176

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The concept of using amide bond distortion to modulate amidic resonance has been known for more than 75 years. Two classic twisted amides (bridged lactams) ingeniously designed and synthesized by Kirby and Stoltz to feature fully perpendicular amide bonds, and as a consequence emanate amino-ketone-like reactivity, are now routinely recognized in all organic chemistry textbooks. However, only recently the use of amide bond twist (distortion) has advanced to the general organic chemistry mainstream enabling a host of highly attractive N-C amide bond cross-coupling reactions of broad synthetic relevance. In this Minireview, we discuss recent progress in this area and present a detailed overview of the prominent role of amide bond destabilization as a driving force in the development of transition-metal-catalyzed cross-coupling reactions by N-C bond activation.

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“…One widely reported approach for the activation of amide bonds involves the distortion of amide bonds, thus, the amide bond is no longer able to form a resonating structure, loses its double bond character, and becomes more susceptible to nucleophilic or electrophilic attack. A higher distortion of the amide bond from the planar structure makes it more reactive, as evidenced by various twisted amide bonds present in cyclic nonplanar bridged lactams, as demonstrated by Stoltz [ 16 , 17 ], Kirby [ 18 , 19 , 20 ], and others [ 21 , 22 , 23 ] ( Figure 2 ). One of the special cases to achieve maximum rotational inversion of the amide bond so that it remains in the twisted conformation is the use of N -acyl-glutarimides [ 24 , 25 , 26 , 27 , 28 , 29 ] and N , N -substituted amide bonds [ 30 , 31 ] ( Figure 2 ).…”

Section: Introductionmentioning

confidence: 99%

Amide Bond Activation of Biological Molecules

2018

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Amide bonds are the most prevalent structures found in organic molecules and various biomolecules such as peptides, proteins, DNA, and RNA. The unique feature of amide bonds is their ability to form resonating structures, thus, they are highly stable and adopt particular three-dimensional structures, which, in turn, are responsible for their functions. The main focus of this review article is to report the methodologies for the activation of the unactivated amide bonds present in biomolecules, which includes the enzymatic approach, metal complexes, and non-metal based methods. This article also discusses some of the applications of amide bond activation approaches in the sequencing of proteins and the synthesis of peptide acids, esters, amides, and thioesters.

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Twisted Amide Analogues of Tröger’s Base

Cited by 34 publications

References 78 publications

Chemistry of Bridged Lactams and Related Heterocycles

Chemistry of Bridged Lactams and Related Heterocycles

Twisted Amides: From Obscurity to Broadly Useful Transition‐Metal‐Catalyzed Reactions by N−C Amide Bond Activation

Amide Bond Activation of Biological Molecules

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