Literature DB >> 21740065

Stereoselective palladium-catalyzed α-arylation of 3-aryl-1-indanones: an asymmetric synthesis of (+)-pauciflorol F.

Bong Hyang Lee1, Young Lok Choi, Seunghoon Shin, Jung-Nyoung Heo.   

Abstract

Highly stereoselective, palladium-catalyzed α-arylation reactions of 3-aryl-1-indanones with aryl bromides are described. The use of sodium tert-butoxide as a base in this process is required to elevate the efficiencies and stereoselectivities of these reactions. The new methodology was successfully applied to a highly efficient route for the asymmetric synthesis of (+)-pauciflorol F.

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Year:  2011        PMID: 21740065     DOI: 10.1021/jo2009164

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  8 in total

Review 1.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

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Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

Review 2.  Chemistry and Biology of Resveratrol-Derived Natural Products.

Authors:  Mitchell H Keylor; Bryan S Matsuura; Corey R J Stephenson
Journal:  Chem Rev       Date:  2015-04-02       Impact factor: 60.622

3.  Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Org Lett       Date:  2021-08-30       Impact factor: 6.072

4.  Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A.

Authors:  Feipeng Liu; Zhe Dong; Jianchun Wang; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-16       Impact factor: 15.336

5.  Synthesis of Vitisins A and D Enabled by a Persistent Radical Equilibrium.

Authors:  Kevin J Romero; Mitchell H Keylor; Markus Griesser; Xu Zhu; Ethan J Strobel; Derek A Pratt; Corey R J Stephenson
Journal:  J Am Chem Soc       Date:  2020-03-24       Impact factor: 15.419

6.  Total Synthesis of Viniferifuran, Resveratrol-Piceatannol Hybrid, Anigopreissin A and Analogues - Investigation of Demethylation Strategies.

Authors:  Duc Duy Vo; Mikael Elofsson
Journal:  Adv Synth Catal       Date:  2016-12-08       Impact factor: 5.837

7.  Efficient kinetic resolution in the asymmetric transfer hydrogenation of 3-aryl-indanones: applications to a short synthesis of (+)-indatraline and a formal synthesis of (R)-tolterodine.

Authors:  Songsoon Park; Hyeon-Kyu Lee
Journal:  RSC Adv       Date:  2021-06-30       Impact factor: 3.361

8.  Synthesis of cis-Oriented Vicinal Diphenylethylenes through a Lewis Acid-Promoted Annulation of Oxotriphenylhexanoates.

Authors:  Martin Kamlar; Elin Henriksson; Ivana Císařová; Marcus Malo; Henrik Sundén
Journal:  J Org Chem       Date:  2021-06-17       Impact factor: 4.354

  8 in total

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