Literature DB >> 19886665

Lewis acid catalyzed inverse-electron-demand Diels-Alder reaction of tropones.

Pingfan Li1, Hisashi Yamamoto.   

Abstract

Lewis acid catalyzed inverse-electron-demand Diels-Alder reaction of tropone derivatives was developed. Up to 97% ee was obtained for the chiral dinucleus BINOL-aluminum complex catalyzed reaction between tropones and ketene diethyl acetal to give bicyclo[3.2.2] ring structures, which opens up a unique way of making chiral seven-membered rings.

Entities:  

Year:  2009        PMID： 19886665      PMCID： PMC2810398          DOI： 10.1021/ja908127f

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


  10 in total

1.  The Absolute Configuration and Asymmetric Total Synthesis of the CP Molecules (CP-263,114 and CP-225,917, Phomoidrides B and A) We thank Drs. D. H. Huang, G. Siuzdak, and R. Chadha for assistance with NMR spectroscopy, mass spectrometry, and X-ray crystallography, respectively. This work was financially supported by the National Institutes of Health (USA), The Skaggs Institute for Chemical Biology, doctoral fellowships from the National Science Foundation (P.S.B.) and Boehringer Ingelheim (Y.H.), and grants from Array Biopharma, Boehringer Ingelheim, Schering Plough, Pfizer, Glaxo, Merck, Hoffmann-La Roche, DuPont, and Abbott Laboratories.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-05-15       Impact factor: 15.336

2.  "Designer acids": combined acid catalysis for asymmetric synthesis.

Authors:  Hisashi Yamamoto; Kentaro Futatsugi
Journal:  Angew Chem Int Ed Engl       Date:  2005-03-18       Impact factor: 15.336

3.  A phosphine-catalyzed [3+6] annulation reaction of modified allylic compounds and tropone.

Authors:  Yishu Du; Jianqing Feng; Xiyan Lu
Journal:  Org Lett       Date:  2005-05-12       Impact factor: 6.005

4.  Lewis Acid-Promoted, Stereocontrolled, Gram Scale, Diels-Alder Cycloadditions of Electronically Matched 2-Pyrones and Vinyl Ethers: The Critical Importance of Molecular Sieves and the Temperature of Titanium Coordination with the Pyrone.

Authors:  Gary H. Posner; Haiyan Dai; D. Scott Bull; Jae-Kyoo Lee; Franck Eydoux; Yuji Ishihara; William Welsh; Neil Pryor; Stan Petr
Journal:  J Org Chem       Date:  1996-01-26       Impact factor: 4.354

5.  Enantioselective Diels-Alder reactions with N-hydroxy-N-phenylacrylamide.

Authors:  Olivier Corminboeuf; Philippe Renaud
Journal:  Org Lett       Date:  2002-05-16       Impact factor: 6.005

6.  Application of Lewis acid catalyzed tropone [6+4] cycloadditions to the synthesis of the core of CP-225,917.

Authors:  L Isakovic; J A Ashenhurst; J L Gleason
Journal:  Org Lett       Date:  2001-12-27       Impact factor: 6.005

7.  Unusual

Authors: 
Journal:  Org Lett       Date:  2000-03-23       Impact factor: 6.005

8.  An N-heterocyclic carbene-catalyzed [8 + 3] annulation of tropone and enals via homoenolate.

Authors:  Vijay Nair; Manojkumar Poonoth; Sreekumar Vellalath; Eringathodi Suresh; Rajasekaran Thirumalai
Journal:  J Org Chem       Date:  2006-11-10       Impact factor: 4.354

9.  Access to a welwitindolinone core using sequential cycloadditions.

Authors:  Barry M Trost; Patrick J McDougall
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

10.  Asymmetric synthesis of bicyclo[4.3.1]decadienes and bicyclo[3.3.2]decadienes via [6 + 3] trimethylenemethane cycloaddition with tropones.

Authors:  Barry M Trost; Patrick J McDougall; Olaf Hartmann; Peter T Wathen
Journal:  J Am Chem Soc       Date:  2008-10-21       Impact factor: 15.419
  10 in total
  8 in total

1.  Synthesis of Naturally Occurring Tropones and Tropolones.

Authors:  Na Liu; Wangze Song; Casi M Schienebeck; Min Zhang; Weiping Tang
Journal:  Tetrahedron       Date:  2014-12-09       Impact factor: 2.457

2.  Silver-catalyzed formal inverse electron-demand Diels-Alder reaction of 1,2-diazines and siloxy alkynes.

Authors:  Yunus E Türkmen; Timothy J Montavon; Sergey A Kozmin; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2012-05-24       Impact factor: 15.419

3.  Enantioselective synthesis of 1,2-dihydronaphthalene-1-carbaldehydes by addition of boronates to isochromene acetals catalyzed by tartaric acid.

Authors:  Yi Luan; Keith S Barbato; Philip N Moquist; Tomohiro Kodama; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2015-02-27       Impact factor: 15.419

4.  Organocatalytic stereoselective [8+2] and [6+4] cycloadditions.

Authors:  Rasmus Mose; Gert Preegel; Jesper Larsen; Sofie Jakobsen; Eva Høgh Iversen; Karl Anker Jørgensen
Journal:  Nat Chem       Date:  2016-12-19       Impact factor: 24.427

5.  Antiaromaticity Gain Activates Tropone and Nonbenzenoid Aromatics as Normal-Electron-Demand Diels-Alder Dienes.

Authors:  Lucas J Karas; Adam T Campbell; Igor V Alabugin; Judy I Wu
Journal:  Org Lett       Date:  2020-08-28       Impact factor: 6.005

6.  Synthesis of Substituted Tropones by Sequential Rh-Catalyzed [5+2] Cycloaddition and Elimination.

Authors:  Wangze Song; Bao-Min Xi; Ka Yang; Weiping Tang
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

7.  Ten years of research in Chicago.

Authors:  Hisashi Yamamoto
Journal:  Tetrahedron       Date:  2013-06-10       Impact factor: 2.457

8.  Ni(NHC)]-catalyzed cycloaddition of diynes and tropone: apparent enone cycloaddition involving an 8π insertion.

Authors:  Puneet Kumar; Ashish Thakur; Xin Hong; K N Houk; Janis Louie
Journal:  J Am Chem Soc       Date:  2014-12-05       Impact factor: 15.419
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.