Literature DB >> 19122868

Applications of the Ugi reaction with ketones.

Suvi T M Simila1, Stephen F Martin.   

Abstract

A convenient synthesis of highly functionalized, α,α-disubstituted amino acid amide derivatives has been accomplished by using cyclic and acyclic ketones as the carbonyl inputs in the Ugi multicomponent reaction. An application of this extension of the Ugi reaction to the synthesis of α,α-divinyl amino acids that may be cyclized via ring-closing metathesis to provide highly substituted pyrrolidines is described.

Entities:  

Year:  2008        PMID: 19122868      PMCID: PMC2516347          DOI: 10.1016/j.tetlet.2008.05.073

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  17 in total

1.  Via Ugi reactions to conformationally fixed cyclic peptides.

Authors:  Christina Hebach; Uli Kazmaier
Journal:  Chem Commun (Camb)       Date:  2003-03-07       Impact factor: 6.222

2.  Multicomponent Reactions with Isocyanides.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-09-15       Impact factor: 15.336

Review 3.  Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis.

Authors:  Alexander Deiters; Stephen F Martin
Journal:  Chem Rev       Date:  2004-05       Impact factor: 60.622

4.  New entry to convertible isocyanides for the Ugi reaction and its application to the stereocontrolled formal total synthesis of the proteasome inhibitor omuralide.

Authors:  Cynthia B Gilley; Matthew J Buller; Yoshihisa Kobayashi
Journal:  Org Lett       Date:  2007-08-02       Impact factor: 6.005

5.  Lewis acid assisted ring-closing metathesis of chiral diallylamines: an efficient approach to enantiopure pyrrolidine derivatives.

Authors:  Qian Yang; Wen-Jing Xiao; Zhengkun Yu
Journal:  Org Lett       Date:  2005-03-03       Impact factor: 6.005

6.  Synthesis of fused bicyclic imidazoles by sequential van Leusen/ring-closing metathesis reactions.

Authors:  Vijaya Gracias; Alan F Gasiecki; Stevan W Djuric
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

7.  Novel anti-tuberculosis agents from MCR libraries.

Authors:  Alexander Dömling; Sepp Achatz; Barbara Beck
Journal:  Bioorg Med Chem Lett       Date:  2007-04-25       Impact factor: 2.823

8.  Biogenetically inspired approach to the Strychnos alkaloids. Concise syntheses of (+/-)-akuammicine and (+/-)-strychnine.

Authors:  M Ito; C W Clark; M Mortimore; J B Goh; S F Martin
Journal:  J Am Chem Soc       Date:  2001-08-22       Impact factor: 15.419

9.  Acid-free, aminoborane-mediated Ugi-type reaction leading to general utilization of secondary amines.

Authors:  Yusuke Tanaka; Tomoaki Hasui; Michinori Suginome
Journal:  Org Lett       Date:  2007-09-22       Impact factor: 6.005

10.  An improved approach for the synthesis of alpha,alpha-dialkyl glycine derivatives by the Ugi-Passerini reaction.

Authors:  Susana P Costa; Hernâni L Maia; Sílvia M Pereira-Lima
Journal:  Org Biomol Chem       Date:  2003-05-07       Impact factor: 3.876

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  4 in total

1.  Intramolecular anodic olefin coupling reactions: use of the reaction rate to control substrate/product selectivity.

Authors:  Hai-Chao Xu; Kevin D Moeller
Journal:  Angew Chem Int Ed Engl       Date:  2010-10-18       Impact factor: 15.336

2.  Intramolecular anodic olefin coupling reactions: using competition studies to probe the mechanism of oxidative cyclization reactions.

Authors:  Hai-Chao Xu; Kevin D Moeller
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

3.  Intramolecular hydroamination of dithioketene acetals: an easy route to cyclic amino acid derivatives.

Authors:  Hai-Chao Xu; Kevin D Moeller
Journal:  Org Lett       Date:  2010-10-14       Impact factor: 6.005

4.  Intramolecular anodic olefin coupling reactions and the synthesis of cyclic amines.

Authors:  Hai-Chao Xu; Kevin D Moeller
Journal:  J Am Chem Soc       Date:  2010-03-03       Impact factor: 15.419

  4 in total

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