Literature DB >> 16492036

Asymmetric synthesis of hydrobenzofuranones via desymmetrization of cyclohexadienones using the intramolecular Stetter reaction.

Qin Liu1, Tomislav Rovis.   

Abstract

Dearomatization of phenols followed by oxidation affords cyclohexadienyloxyacetaldehydes, which produce hydrobenzofuranones via asymmetric intramolecular Stetter reaction in good to excellent yield. Quaternary as well as up to three contiguous stereocenters may be formed in good to excellent enantioselectivities and high diastereoselectivities.

Entities:  

Mesh:

Substances:

Year:  2006        PMID: 16492036      PMCID: PMC2701296          DOI: 10.1021/ja058337u

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  23 in total

1.  A highly enantioselective intramolecular Heck reaction with a monodentate ligand.

Authors:  Rosalinde Imbos; Adriaan J Minnaard; Ben L Feringa
Journal:  J Am Chem Soc       Date:  2002-01-16       Impact factor: 15.419

2.  First total synthesis of (+/-)-Linderol A, a tricyclic hexahydrodibenzofuran constituent of Lindera umbellata bark, with potent inhibitory activity on melanin biosynthesis of cultured B-16 melanoma cells.

Authors:  Masayuki Yamashita; Nobukazu Ohta; Takashi Shimizu; Kayoko Matsumoto; Yoko Matsuura; Ikuo Kawasaki; Tetsuaki Tanaka; Naoyoshi Maezaki; Shunsaku Ohta
Journal:  J Org Chem       Date:  2003-02-21       Impact factor: 4.354

3.  A rapid stereocontrolled entry to the ABCD tetracyclic core of neotuberostemonine.

Authors:  Kevin I Booker-Milburn; Paul Hirst; Jonathan P H Charmant; Luke H J Taylor
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-11       Impact factor: 15.336

4.  New cyclohexadienone derivatives: preparation and chiral discrimination in high-pressure Diels-Alder cycloadditions.

Authors:  M E Trân-Huu-Dâu; R Wartchow; E Winterfeldt; Y S Wong
Journal:  Chemistry       Date:  2001-06-01       Impact factor: 5.236

5.  Extending mechanistic routes in heterazolium catalysis--promising concepts for versatile synthetic methods.

Authors:  Kirsten Zeitler
Journal:  Angew Chem Int Ed Engl       Date:  2005-11-25       Impact factor: 15.336

6.  Nitrogenous educts through oxidative amidation of phenols: the bimolecular reaction.

Authors:  Sylvain Canesi; Denis Bouchu; Marco A Ciufolini
Journal:  Org Lett       Date:  2005-01-20       Impact factor: 6.005

7.  An enantioselective route to paeonilactone A via palladium- and copper-catalyzed reactions.

Authors:  C Jonasson; M Rönn; J E Bäckvall
Journal:  J Org Chem       Date:  2000-04-07       Impact factor: 4.354

8.  Synthesis of (-)-morphine.

Authors:  Douglass F Taber; Timothy D Neubert; Arnold L Rheingold
Journal:  J Am Chem Soc       Date:  2002-10-23       Impact factor: 15.419

9.  Total Synthesis of (R)-Dihydroactinidiolide and (R)-Actinidiolide Using Asymmetric Catalytic Hetero-Diels-Alder Methodology.

Authors:  Sulan Yao; Mogens Johannsen; Rita G. Hazell; Karl Anker Jørgensen
Journal:  J Org Chem       Date:  1998-01-09       Impact factor: 4.354

10.  Synthesis of (+)-nocardione A--use of formal radical cyclization onto a benzene ring.

Authors:  Derrick L J Clive; Stephen P Fletcher
Journal:  Chem Commun (Camb)       Date:  2003-10-07       Impact factor: 6.222

View more
  27 in total

1.  Enantioselective synthesis of hindered cyclic dialkyl ethers via catalytic oxa-Michael/Michael desymmetrization.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  Chem Sci       Date:  2013-07-01       Impact factor: 9.825

Review 2.  Carbene catalysts.

Authors:  Jennifer L Moore; Tomislav Rovis
Journal:  Top Curr Chem       Date:  2010

3.  An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.

Authors:  David M Rubush; Michelle A Morges; Barbara J Rose; Douglas H Thamm; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-08-07       Impact factor: 15.419

4.  Mechanistic investigation of the enantioselective intramolecular stetter reaction: proton transfer is the first irreversible step.

Authors:  Jennifer L Moore; Anthony P Silvestri; Javier Read de Alaniz; Daniel A DiRocco; Tomislav Rovis
Journal:  Org Lett       Date:  2011-02-28       Impact factor: 6.005

5.  Asymmetric N-Heterocyclic Carbene (NHC) Catalyzed Acyl Anion Reactivity.

Authors:  Harit U Vora; Tomislav Rovis
Journal:  Aldrichimica Acta       Date:  2011       Impact factor: 3.667

6.  Experimental and Computational Gas Phase Acidities of Conjugate Acids of Triazolylidene Carbenes: Rationalizing Subtle Electronic Effects.

Authors:  Yijie Niu; Ning Wang; Alberto Muñoz; Jiahui Xu; Hao Zeng; Tomislav Rovis; Jeehiun K Lee
Journal:  J Am Chem Soc       Date:  2017-10-17       Impact factor: 15.419

7.  The Catalytic Asymmetric Intramolecular Stetter Reaction.

Authors:  Javier Read de Alaniz; Tomislav Rovis
Journal:  Synlett       Date:  2009-05       Impact factor: 2.454

8.  Enantioselective Synthesis of Hydrobenzofuranones Using an Asymmetric Desymmetrizing Intramolecular Stetter Reaction of Cyclohexadienones.

Authors:  Qin Liu; Tomislav Rovis
Journal:  Org Process Res Dev       Date:  2007       Impact factor: 3.317

9.  Nucleophilic carbene catalyzed synthesis of 1,2 amino alcohols via azidation of epoxy aldehydes.

Authors:  Harit U Vora; Johannah R Moncecchi; Oleg Epstein; Tomislav Rovis
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

10.  Enantioselective synthesis of alpha,alpha-disubstituted cyclopentenes by an N-heterocyclic carbene-catalyzed desymmetrization of 1,3-diketones.

Authors:  Manabu Wadamoto; Eric M Phillips; Troy E Reynolds; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-07-31       Impact factor: 15.419

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.