Literature DB >> 24838340

Catalytic enantioselective Nazarov cyclization: construction of vicinal all-carbon-atom quaternary stereocenters.

Anais Jolit1, Patrick M Walleser, Glenn P A Yap, Marcus A Tius.   

Abstract

The diastereoselective asymmetric synthesis of vicinal all-carbon-atom quaternary stereocenters is a challenging problem in organic synthesis for which only few solutions have been described. A catalytic asymmetric Nazarov cyclization of fully substituted dienones that provides cyclopentenone derivatives with vicinal quaternary stereocenters in high optical purity and as single diastereoisomers is now reported.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Nazarov cyclization; asymmetric catalysis; chiral Brønsted acids; quaternary stereocenters

Mesh：

Substances：

Year:  2014        PMID： 24838340     DOI： 10.1002/anie.201403587

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  13 in total

1.  Iridium-Catalyzed Stereoselective Allylic Alkylation Reactions with Crotyl Chloride.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-28       Impact factor: 15.336

2.  Formation of DPM ethers using O-diphenylmethyl trichloroacetimidate under thermal conditions.

Authors:  Kyle T Howard; Brian C Duffy; Matthew R Linaburg; John D Chisholm
Journal:  Org Biomol Chem       Date:  2016-02-07       Impact factor: 3.876

3.  Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-11       Impact factor: 15.336

4.  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

5.  Crellasterones A and B: A-Norsterol Derivatives from the New Caledonian Sponge Crella incrustans.

Authors:  Kavita Ragini; Andrew M Piggott; Peter Karuso
Journal:  Mar Drugs       Date:  2017-06-15       Impact factor: 5.118

6.  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

7.  Optimization of Nazarov Cyclization of 2,4-Dimethyl-1,5-diphenylpenta-1,4-dien-3-one in Deep Eutectic Solvents by a Design of Experiments Approach.

Authors:  Stefano Nejrotti; Alberto Mannu; Marco Blangetti; Salvatore Baldino; Andrea Fin; Cristina Prandi
Journal:  Molecules       Date:  2020-12-04       Impact factor: 4.411

Review 8.  Catalytic enantioselective construction of vicinal quaternary carbon stereocenters.

Authors:  Feng Zhou; Lei Zhu; Bo-Wen Pan; Yang Shi; Yun-Lin Liu; Jian Zhou
Journal:  Chem Sci       Date:  2020-07-28       Impact factor: 9.825

9.  Asymmetric synthesis of multiple quaternary stereocentre-containing cyclopentyls by oxazolidinone-promoted Nazarov cyclizations.

Authors:  Rohan Volpe; Romain J Lepage; Jonathan M White; Elizabeth H Krenske; Bernard L Flynn
Journal:  Chem Sci       Date:  2018-04-20       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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