Literature DB >> 15724183

A peptide-catalyzed asymmetric Stetter reaction.

Steven M Mennen1, Jarred T Blank, Michelle B Tran-Dubé, Jason E Imbriglio, Scott J Miller.   

Abstract

Thiazolylalanine, in appropriately functionalized form, has been found to function as an enantioselective catalyst for an intramolecular Stetter reaction. Incorporation of the residue in a number of environments has resulted in a family of catalysts that promote the cyclization of a test substrate with up to 81% enantiomeric excess.

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Year:  2004        PMID: 15724183     DOI: 10.1039/b414574g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  14 in total

1.  An efficient synthesis of achiral and chiral 1,2,4-triazolium salts: bench stable precursors for N-heterocyclic carbenes.

Authors:  Mark S Kerr; Javier Read de Alaniz; Tomislav Rovis
Journal:  J Org Chem       Date:  2005-07-08       Impact factor: 4.354

Review 2.  Carbene catalysts.

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

Review 3.  The Cation-π Interaction in Small-Molecule Catalysis.

Authors:  C Rose Kennedy; Song Lin; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-22       Impact factor: 15.336

4.  Metallophosphite-induced nucleophilic acylation of alpha,beta-unsaturated amides: facilitated catalysis by a diastereoselective retro [1,4] Brook rearrangement.

Authors:  Mary R Nahm; Xin Linghu; Justin R Potnick; Christopher M Yates; Peter S White; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2005-04-15       Impact factor: 15.336

5.  The Catalytic Asymmetric Intramolecular Stetter Reaction.

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

6.  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

7.  Metallophosphite-catalyzed asymmetric acylation of alpha,beta-unsaturated amides.

Authors:  Mary R Nahm; Justin R Potnick; Peter S White; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

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

Authors:  Qin Liu; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

9.  Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates.

Authors:  Qin Liu; Stéphane Perreault; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2008-10-04       Impact factor: 15.419

10.  Enantio- and diastereoselective intermolecular Stetter reaction of glyoxamide and alkylidene ketoamides.

Authors:  Qin Liu; Tomislav Rovis
Journal:  Org Lett       Date:  2009-07-02       Impact factor: 6.005

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