Literature DB >> 28262863

Asymmetric organocatalytic methods for the synthesis of tetrahydropyrans and their application in total synthesis.

Fabrizio Vetica1, Pankaj Chauhan1, Simon Dochain1, Dieter Enders1.   

Abstract

Recent advancement in the area of asymmetric organocatalysis led to the development of new methodologies for the construction of valuable enantiopure molecules, including various heterocycles. As one of the latter class of compounds tetrahydropyrans (THPs) constitute a core structure of a wide array of bioactive natural products. A noticeable growth has been observed in the asymmetric synthesis of THPs using small organic molecules as catalysts. This Tutorial Review describes the organocatalytic methods available to furnish THPs as well as the application of these methodologies in the total synthesis of THP-based natural products.

Entities:  

Year:  2017        PMID: 28262863     DOI: 10.1039/c6cs00757k

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  9 in total

1.  An Enantioselective Cross-Dehydrogenative Coupling Catalysis Approach to Substituted Tetrahydropyrans.

Authors:  Ansoo Lee; Rick C Betori; Erika A Crane; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2018-05-10       Impact factor: 15.419

2.  Investigations towards the stereoselective organocatalyzed Michael addition of dimethyl malonate to a racemic nitroalkene: possible route to the 4-methylpregabalin core structure.

Authors:  Denisa Vargová; Rastislav Baran; Radovan Šebesta
Journal:  Beilstein J Org Chem       Date:  2018-03-05       Impact factor: 2.883

3.  Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives.

Authors:  Zheng-Yi Li; Hong-Xiao Tong; Yuan Chen; Hong-Kui Su; Tangxin Xiao; Xiao-Qiang Sun; Leyong Wang
Journal:  Beilstein J Org Chem       Date:  2018-07-25       Impact factor: 2.883

4.  An Enamide-Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans.

Authors:  Philipp Kramer; Jennifer Grimmer; Michael Bolte; Georg Manolikakes
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-07       Impact factor: 15.336

Review 5.  An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies.

Authors:  Qili Lu; Dipesh S Harmalkar; Yongseok Choi; Kyeong Lee
Journal:  Molecules       Date:  2019-10-21       Impact factor: 4.411

Review 6.  Synthetic and biosynthetic methods for selective cyclisations of 4,5-epoxy alcohols to tetrahydropyrans.

Authors:  James I Bowen; Luoyi Wang; Matthew P Crump; Christine L Willis
Journal:  Org Biomol Chem       Date:  2022-02-09       Impact factor: 3.876

7.  H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters.

Authors:  Patryk Niedbała; Maciej Majdecki; Piotr Grodek; Janusz Jurczak
Journal:  Molecules       Date:  2022-04-13       Impact factor: 4.927

8.  Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael-Domino Michael/Aldol Reaction.

Authors:  Leonardo Straminelli; Francesco Vicentini; Antonio Di Sabato; Carmela Maria Montone; Chiara Cavaliere; Kari Rissanen; Francesca Leonelli; Fabrizio Vetica
Journal:  J Org Chem       Date:  2022-07-25       Impact factor: 4.198

9.  Electrochemical Bottom-Up Synthesis of Chiral Carbon Dots from L-Proline and Their Application as Nano-Organocatalysts in a Stereoselective Aldol Reaction.

Authors:  Martina Bortolami; Ingrid Izabela Bogles; Cecilia Bombelli; Fabiana Pandolfi; Marta Feroci; Fabrizio Vetica
Journal:  Molecules       Date:  2022-08-12       Impact factor: 4.927

  9 in total

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