Literature DB >> 18341346

Regio- and enantioselective catalytic cyclization of pyrroles onto N-acyliminium ions.

Izzat T Raheem1, Parvinder S Thiara, Eric N Jacobsen.   

Abstract

The regio- and enantioselective cyclization of pyrroles onto N-acyliminium ions generated in situ from hydroxylactams is reported. Modest to excellent ee's and yields are obtained in these novel Pictet-Spengler-type reactions with a chiral thiourea-pyrrole catalyst. Useful synthetic transformations of the versatile pyrroloindolizidinone and pyrroloquinolizidinone products are presented.

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Year:  2008        PMID： 18341346     DOI： 10.1021/ol800256j

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  19 in total

Review 1.  Natural products as inspiration for the development of asymmetric catalysis.

Authors:  Justin T Mohr; Michael R Krout; Brian M Stoltz
Journal:  Nature       Date:  2008-09-18       Impact factor: 49.962

2.  On- and Off-Cycle Catalyst Cooperativity in Anion-Binding Catalysis.

Authors:  David D Ford; Dan Lehnherr; C Rose Kennedy; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-06-15       Impact factor: 15.419

3.  Enantioselective Pictet-Spengler Reactions of Isatins for the Synthesis of Spiroindolones.

Authors:  Joseph J Badillo; Abel Silva-García; Benjamin H Shupe; James C Fettinger; Annaliese K Franz
Journal:  Tetrahedron Lett       Date:  2011-10-26       Impact factor: 2.415

4.  The progression of chiral anions from concepts to applications in asymmetric catalysis.

Authors:  Robert J Phipps; Gregory L Hamilton; F Dean Toste
Journal:  Nat Chem       Date:  2012-07-24       Impact factor: 24.427

5.  Enantioselective thiourea-catalyzed cationic polycyclizations.

Authors:  Robert R Knowles; Song Lin; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2010-04-14       Impact factor: 15.419

6.  Chiral Thioureas Promote Enantioselective Pictet-Spengler Cyclization by Stabilizing Every Intermediate and Transition State in the Carboxylic Acid-Catalyzed Reaction.

Authors:  Rebekka S Klausen; C Rose Kennedy; Alan M Hyde; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2017-08-22       Impact factor: 15.419

7.  Development of the Vinylogous Pictet-Spengler Cyclization and Total Synthesis of (±)-Lundurine A.

Authors:  Aaron Nash; Xiangbing Qi; Pradip Maity; Kyle Owens; Uttam K Tambar
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-04       Impact factor: 15.336

8.  Xanthene-4,5-diamine derivatives: a study of anion-binding catalysis.

Authors:  Alison E Metz; Kailasham Ramalingam; Marisa C Kozlowski
Journal:  Tetrahedron Lett       Date:  2015-09-09       Impact factor: 2.415

9.  Enantioselective, thiourea-catalyzed intermolecular addition of indoles to cyclic N-acyl iminium ions.

Authors:  Emily A Peterson; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 10.  Asymmetric ion-pairing catalysis.

Authors:  Katrien Brak; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-28       Impact factor: 15.336
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