Literature DB >> 27101336

Synthesis of Chiral Cyclopentenones.

Svilen P Simeonov1, João P M Nunes2, Krassimira Guerra3, Vanya B Kurteva1, Carlos A M Afonso3.   

Abstract

The cyclopentenone unit is a very powerful synthon for the synthesis of a variety of bioactive target molecules. This is due to the broad diversity of chemical modifications available for the enone structural motif. In particular, chiral cyclopentenones are important precursors in the asymmetric synthesis of target chiral molecules. This Review provides an overview of reported methods for enantioselective and asymmetric syntheses of cyclopentenones, including chemical and enzymatic resolution, asymmetric synthesis via Pauson-Khand reaction, Nazarov cyclization and organocatalyzed reactions, asymmetric functionalization of the existing cyclopentenone unit, and functionalization of chiral building blocks.

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Year:  2016        PMID: 27101336     DOI: 10.1021/cr500504w

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  12 in total

1.  Substituted α-Alkylidene Cyclopentenones via the Intramolecular Reaction of Vinyl Cations with Alkenes.

Authors:  Magenta J Hensinger; Nicholas J Dodge; Matthias Brewer
Journal:  Org Lett       Date:  2019-12-24       Impact factor: 6.005

2.  Migratory Aptitudes in Rearrangements of Destabilized Vinyl Cations.

Authors:  Sarah E Cleary; Magenta J Hensinger; Zhi-Xin Qin; Xin Hong; Matthias Brewer
Journal:  J Org Chem       Date:  2019-11-20       Impact factor: 4.354

3.  Enantioselective Nazarov cyclization of indole enones cooperatively catalyzed by Lewis acids and chiral Brønsted acids.

Authors:  Guo-Peng Wang; Meng-Qing Chen; Shou-Fei Zhu; Qi-Lin Zhou
Journal:  Chem Sci       Date:  2017-08-29       Impact factor: 9.825

4.  Remote C-H insertion of vinyl cations leading to cyclopentenones.

Authors:  Sarah E Cleary; Magenta J Hensinger; Matthias Brewer
Journal:  Chem Sci       Date:  2017-08-03       Impact factor: 9.825

5.  Strong and Confined Acids Enable a Catalytic Asymmetric Nazarov Cyclization of Simple Divinyl Ketones.

Authors:  Jie Ouyang; Jennifer L Kennemur; Chandra Kanta De; Christophe Farès; Benjamin List
Journal:  J Am Chem Soc       Date:  2019-02-15       Impact factor: 15.419

6.  Total synthesis and antimicrobial evaluation of (+)-hygrophorone B12 and its analogues.

Authors:  Takaaki Kamishima; Masato Suzuki; Koichi Narita; Yoshitaka Koseki; Toshiyuki Nonaka; Hirotaka Nakatsuji; Hideo Hattori; Hitoshi Kasai
Journal:  Sci Rep       Date:  2022-05-06       Impact factor: 4.996

7.  Substrate-controlled selectivity switch in a three-component reaction: sequential synthesis of spiro-oxazolidinedione-cyclopentenones and hydroxy enaminobarbiturates in water.

Authors:  Mohammad Bagher Teimouri; Mahdi Heydari; Kazem Mohammadi
Journal:  RSC Adv       Date:  2020-04-03       Impact factor: 4.036

8.  Synthesis, functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent.

Authors:  Talal F Al-Azemi; Mickey Vinodh; Fatemeh H Alipour; Abdirahman A Mohamod
Journal:  RSC Adv       Date:  2019-07-26       Impact factor: 4.036

9.  Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals.

Authors:  Hongze Liao; Wei-Lin Leng; Kim Le Mai Hoang; Hui Yao; Jingxi He; Amanda Ying Hui Voo; Xue-Wei Liu
Journal:  Chem Sci       Date:  2017-08-07       Impact factor: 9.825

10.  Enantioselective Synthesis of Chiral Cyclopent-2-enones by Nickel-Catalyzed Desymmetrization of Malonate Esters.

Authors:  Somnath Narayan Karad; Heena Panchal; Christopher Clarke; William Lewis; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-19       Impact factor: 15.336

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