Literature DB >> 20958040

Synthesis of amino acid derived enaminones via Wolff rearrangement using vinylogous amides as carbon nucleophiles.

Hajime Seki1, Gunda I Georg.   

Abstract

Cyclic enaminones were synthesized in high yields from amino acids in two steps via Wolff rearrangement. The cyclization represents a rare 6-exo-dig cyclization involving a ketene as an electrophile. No racemization was observed during this reaction.

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Year:  2010        PMID： 20958040      PMCID： PMC2974010          DOI： 10.1021/ja107329k

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


  8 in total

1.  Catalytic enantioselective aza-Diels-alder reactions of imines--an approach to optically active nonproteinogenic alpha-amino acids

Authors: 
Journal:  Chemistry       Date:  2000-07-03       Impact factor: 5.236

2.  Amino acid-derived enaminones: a study in ring formation providing valuable asymmetric synthons.

Authors:  Brandon J Turunen; Gunda I Georg
Journal:  J Am Chem Soc       Date:  2006-07-12       Impact factor: 15.419

Review 3.  Synthetic applications of chiral 2,3-dihydro-4-pyridones.

Authors:  Sajan Joseph; Daniel L Comins
Journal:  Curr Opin Drug Discov Devel       Date:  2002-11

4.  Efficient and practical Ag-catalyzed cycloadditions between arylimines and the Danishefsky diene.

Authors:  Nathan S Josephsohn; Marc L Snapper; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2003-04-09       Impact factor: 15.419

5.  Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine.

Authors:  Micah J Niphakis; Gunda I Georg
Journal:  J Org Chem       Date:  2010-09-03       Impact factor: 4.354

6.  Phenanthroindolizidines and Phenanthroquinolizidines: Promising Alkaloids for Anti-Cancer Therapy.

Authors:  Sherry R Chemler
Journal:  Curr Bioact Compd       Date:  2009-03-01

7.  Chiral copper complexes of phosphino sulfenyl ferrocenes as efficient catalysts for enantioselective formal Aza Diels-Alder reactions of N-sulfonyl imines.

Authors:  Olga García Mancheño; Ramón Gómez Arrayás; Juan C Carretero
Journal:  J Am Chem Soc       Date:  2004-01-21       Impact factor: 15.419

Review 8.  Indolizidine and quinolizidine alkaloids.

Authors:  Joseph P Michael
Journal:  Nat Prod Rep       Date:  2007-12-13       Impact factor: 13.423
  8 in total
  11 in total

1.  Enantiospecific Synthesis and Biological Investigations of a Nuphar Alkaloid: Proposed Structure of a Castoreum Component.

Authors:  Hajime Seki; Gunda I Georg
Journal:  European J Org Chem       Date:  2014-06-01

2.  Three-component synthesis of cyclic enaminones via ketene cyclization.

Authors:  Hajime Seki; Gunda I Georg
Journal:  Org Lett       Date:  2011-04-01       Impact factor: 6.005

3.  Enantioselective Aza-Sakurai Cyclizations: Dual Role of Thiourea as H-Bond Donor and Lewis Base.

Authors:  Yongho Park; Corinna S Schindler; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-11-03       Impact factor: 15.419

4.  Vinylogous reactivity of enol diazoacetates with donor-acceptor substituted hydrazones. Synthesis of substituted pyrazole derivatives.

Authors:  Xinfang Xu; Peter Y Zavalij; Wenhao Hu; Michael P Doyle
Journal:  J Org Chem       Date:  2013-01-24       Impact factor: 4.354

5.  Copper-assisted palladium(II)-catalyzed direct arylation of cyclic enaminones with arylboronic acids.

Authors:  Yong Wook Kim; Micah J Niphakis; Gunda I Georg
Journal:  J Org Chem       Date:  2012-10-22       Impact factor: 4.354

6.  A Photochemical Two-Step Formal [5+2] Cycloaddition: A Condensation/Ring-Expansion Approach to Substituted Azepanes.

Authors:  Scott M Thullen; David M Rubush; Tomislav Rovis
Journal:  Synlett       Date:  2017-06-29       Impact factor: 2.454

7.  Total synthesis of (-)-epimyrtine by a gold-catalyzed hydroamination approach.

Authors:  Thi Thanh Huyen Trinh; Khanh Hung Nguyen; Patricia de Aguiar Amaral; Nicolas Gouault
Journal:  Beilstein J Org Chem       Date:  2013-10-09       Impact factor: 2.883

8.  Organocatalytic activation of isocyanides: N-heterocyclic carbene-catalyzed enaminone synthesis from ketones.

Authors:  Jungwon Kim; Soon Hyeok Hong
Journal:  Chem Sci       Date:  2016-12-20       Impact factor: 9.825

9.  Efficient PPA-SiO2-catalyzed synthesis of β-enaminones under solvent-free conditions.

Authors:  Muhammad Nisar; Ihsan Ali; Muhammad Raza Shah; Mughal Qayum; Muhammad Zia-Ul-Haq; Umer Rashid; Md Saiful Islam
Journal:  Molecules       Date:  2013-12-10       Impact factor: 4.411

10.  Formal oxo- and aza-[3 + 2] reactions of α-enaminones and quinones: a double divergent process and the roles of chiral phosphoric acid and molecular sieves.

Authors:  Weiwei Luo; Zhicheng Sun; E H Nisala Fernando; Vladimir N Nesterov; Thomas R Cundari; Hong Wang
Journal:  Chem Sci       Date:  2020-07-09       Impact factor: 9.825
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