Literature DB >> 16939246

Catalytic enantioselective decarboxylative protonation.

Justin T Mohr1, Toyoki Nishimata, Douglas C Behenna, Brian M Stoltz.   

Abstract

We report a highly enantioselective, general catalytic system for the facile synthesis of tertiary stereocenters by protonation adjacent to cyclic ketones. The method relies on catalytic decarboxylative protonation of readily accessible racemic quaternary beta-ketoesters. A range of substituted cycloalkanone compounds can be accessed through this process with high levels of enantioselectivity.

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Year:  2006        PMID: 16939246     DOI: 10.1021/ja063335a

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


  29 in total

1.  Mechanistic origin of the stereodivergence in decarboxylative allylation.

Authors:  Kalicharan Chattopadhyay; Ranjan Jana; Victor W Day; Justin T Douglas; Jon A Tunge
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

Review 2.  Enantioselective protonation.

Authors:  Justin T Mohr; Allen Y Hong; Brian M Stoltz
Journal:  Nat Chem       Date:  2009-08       Impact factor: 24.427

3.  Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides.

Authors:  Nolan T McDougal; Jan Streuff; Herschel Mukherjee; Scott C Virgil; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2010-10-20       Impact factor: 2.415

4.  Catalytic enantioselective stereoablative reactions: an unexploited approach to enantioselective catalysis.

Authors:  Justin T Mohr; David C Ebner; Brian M Stoltz
Journal:  Org Biomol Chem       Date:  2007-10-01       Impact factor: 3.876

Review 5.  Enantioselective Tsuji allylations.

Authors:  Justin T Mohr; Brian M Stoltz
Journal:  Chem Asian J       Date:  2007-12-03

6.  Direct, iridium-catalyzed enantioselective and regioselective allylic etherification with aliphatic alcohols.

Authors:  Satoshi Ueno; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

7.  The catalytic asymmetric total synthesis of elatol.

Authors:  David E White; Ian C Stewart; Robert H Grubbs; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2007-12-29       Impact factor: 15.419

8.  Asymmetric Protonation of Cumulenolates: Synthesis of Allenyl Aldehydes Facilitated by an Organomanganese Auxiliary.

Authors:  Animesh Roy; Bilal A Bhat; Salvatore D Lepore
Journal:  Org Lett       Date:  2016-02-29       Impact factor: 6.005

9.  PREPARATION OF (S)-tert-ButylPHOX (Oxazole, 4-(1,1-dimethylethyl)-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro- (4S)-).

Authors:  Michael R Krout; Justin T Mohr; Brian M Stoltz
Journal:  Organic Synth       Date:  2009-01-01

10.  Synthesis and Exploration of Electronically Modified (R)-5,5-Dimethyl-(p-CF3)3-i-PrPHOX in Palladium-Catalyzed Enantio- and Diastereoselective Allylic Alkylation: A Practical Alternative to (R)-(p-CF3)3-t-BuPHOX.

Authors:  Robert A Craig; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2015-08-05       Impact factor: 2.415

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