Literature DB >> 34406005

Acyclic Twisted Amides.

Guangrong Meng1, Jin Zhang1,2, Michal Szostak1.   

Abstract

In this contribution, we provide a comprehensive overview of acyclic twisted amides, covering the literature since 1993 (the year of the first recognized report on acyclic twisted amides) through June 2020. The review focuses on classes of acyclic twisted amides and their key structural properties, such as amide bond twist and nitrogen pyramidalization, which are primarily responsible for disrupting nN to π*C═O conjugation. Through discussing acyclic twisted amides in comparison with the classic bridged lactams and conformationally restricted cyclic fused amides, the reader is provided with an overview of amidic distortion that results in novel conformational features of acyclic amides that can be exploited in various fields of chemistry ranging from organic synthesis and polymers to biochemistry and structural chemistry and the current position of acyclic twisted amides in modern chemistry.

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Year:  2021        PMID： 34406005      PMCID： PMC9108997          DOI： 10.1021/acs.chemrev.1c00225

Source DB:  PubMed          Journal:  Chem Rev        ISSN： 0009-2665            Impact factor:   72.087


  260 in total

1.  An N,N'-diamidocarbene: studies in C-H insertion, reversible carbonylation, and transition-metal coordination chemistry.

Authors:  Todd W Hudnall; Christopher W Bielawski
Journal:  J Am Chem Soc       Date:  2009-11-11       Impact factor: 15.419

2.  New class of pyridine catalyst having a conformation switch system: asymmetric acylation of various sec-alcohols.

Authors:  Shinji Yamada; Tomoko Misono; Yuko Iwai; Ayako Masumizu; Yukiko Akiyama
Journal:  J Org Chem       Date:  2006-09-01       Impact factor: 4.354

3.  Ground-State Distortion in N-Acyl-tert-butyl-carbamates (Boc) and N-Acyl-tosylamides (Ts): Twisted Amides of Relevance to Amide N-C Cross-Coupling.

Authors:  Roman Szostak; Shicheng Shi; Guangrong Meng; Roger Lalancette; Michal Szostak
Journal:  J Org Chem       Date:  2016-08-02       Impact factor: 4.354

4.  Enhanced reactivity of twisted amides inside a molecular cage.

Authors:  Hiroki Takezawa; Kosuke Shitozawa; Makoto Fujita
Journal:  Nat Chem       Date:  2020-04-20       Impact factor: 24.427

5.  Catalytic, enantioselective bifunctional inverse electron demand hetero-Diels-Alder reactions of ketene enolates and o-benzoquinone diimides.

Authors:  Ciby J Abraham; Daniel H Paull; Michael T Scerba; James W Grebinski; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2006-10-18       Impact factor: 15.419

6.  N-Acylcarbazoles and N-Acylindoles: Electronically Activated Amides for N-C(O) Cross-Coupling by Nlp to Ar Conjugation Switch.

Authors:  Jonathan Buchspies; Md Mahbubur Rahman; Roman Szostak; Michal Szostak
Journal:  Org Lett       Date:  2020-06-01       Impact factor: 6.005

7.  Practical synthesis of (R)-4-mercaptopyrrolidine-2-thione from L-aspartic acid. Preparation of a novel orally active 1-beta-methylcarbapenem, TA-949.

Authors:  M Seki; T Yamanaka; K Kondo
Journal:  J Org Chem       Date:  2000-01-28       Impact factor: 4.354

8.  An efficient computational model to predict protonation at the amide nitrogen and reactivity along the C-N rotational pathway.

Authors:  Roman Szostak; Jeffrey Aubé; Michal Szostak
Journal:  Chem Commun (Camb)       Date:  2015-04-14       Impact factor: 6.222

9.  Palladium-catalyzed intramolecular C-arylation of benzylic carbon: synthesis of 3-benzoxazolylisoindolinones by a sequence of Ugi-4CR/postfunctionalization.

Authors:  Angela Salcedo; Luc Neuville; Jieping Zhu
Journal:  J Org Chem       Date:  2008-04-02       Impact factor: 4.354

10.  1-Acetyl-4-phenyl-5a,6,7,8,9,9a-hexa-hydro-5H-1,5-benzodiazepin-2(1H)-one.

Authors:  Hanane Benzeid; Nathalie Saffon; Bernard Garrigues; El Mokhtar Essassi; Seik Weng Ng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-07
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  6 in total

1.  Structures of the Most Twisted Thioamide and Selenoamide: Effect of Higher Chalcogens of Twisted Amides on N-C(X) Resonance.

Authors:  Qun Zhao; Guangchen Li; Pradeep Nareddy; Frank Jordan; Roger Lalancette; Roman Szostak; Michal Szostak
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-26       Impact factor: 16.823

2.  An economical approach for peptide synthesis via regioselective C-N bond cleavage of lactams.

Authors:  Wataru Muramatsu; Hisashi Yamamoto
Journal:  Chem Sci       Date:  2022-04-26       Impact factor: 9.969

Review 3.  Synthesis of Natural Products by C-H Functionalization of Heterocycless.

Authors:  Yang Zhang; Michal Szostak
Journal:  Chemistry       Date:  2022-02-17       Impact factor: 5.020

4.  Decarbonylative Sonogashira Cross-Coupling: Fruitful Marriage of Alkynes with Carboxylic Acid Electrophiles.

Authors:  Chengwei Liu; Michal Szostak
Journal:  Org Chem Front       Date:  2021-11-19       Impact factor: 5.456

5.  Nickel-catalyzed skeletal transformation of tropone derivatives via C-C bond activation: catalyst-controlled access to diverse ring systems.

Authors:  Takuya Kodama; Kanako Saito; Mamoru Tobisu
Journal:  Chem Sci       Date:  2022-04-04       Impact factor: 9.969

Review 6.  The Chemical Relationship Among Beta-Lactam Antibiotics and Potential Impacts on Reactivity and Decomposition.

Authors:  Jonathan Turner; Alyssa Muraoka; Michael Bedenbaugh; Blaine Childress; Lauren Pernot; Mark Wiencek; Yuri K Peterson
Journal:  Front Microbiol       Date:  2022-03-24       Impact factor: 5.640
  6 in total

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