Literature DB >> 15524484

Catalytic additions of acylsilanes to imines: an acyl anion strategy for the direct synthesis of alpha-amino ketones.

Anita E Mattson1, Karl A Scheidt.   

Abstract

The addition of acylsilanes to imines catalyzed by neutral carbenes (or zwitterions) generated in situ from readily available thiazolium salts is described. The general reaction successfully utilizes acylsilanes as carbonyl anion precursors and is tolerant of a range of structural diversity on the acylsilane or imine electrophile. The overall reaction utilizes easily available precursors and directly accesses protected alpha-amino ketones in the correct oxidation state.

Entities:  

Year:  2004        PMID： 15524484     DOI： 10.1021/ol0481129

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


  12 in total

1.  Discovering New Reactions with N-Heterocyclic Carbene Catalysis.

Authors:  Eric M Phillips; Audrey Chan; Karl A Scheidt
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

2.  Highly stereoselective formal [3 + 3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes.

Authors:  Audrey Chan; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-04-04       Impact factor: 15.419

Review 3.  Carbene catalysts.

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

4.  A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes.

Authors:  Eric M Phillips; Manabu Wadamoto; Audrey Chan; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Enantioselective metallophosphite-catalyzed C-acylation of nitrones.

Authors:  Mary R Garrett; James C Tarr; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2007-10-10       Impact factor: 15.419

6.  Protonation of Homoenolate Equivalents Generated by N-Heterocyclic Carbenes.

Authors:  Brooks E Maki; Audrey Chan; Karl A Scheidt
Journal:  Synthesis (Stuttg)       Date:  2008-04       Impact factor: 3.157

7.  Nucleophilic acylation of o-quinone methides: an umpolung strategy for the synthesis of alpha-aryl ketones and benzofurans.

Authors:  Anita E Mattson; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-03-23       Impact factor: 15.419

8.  Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.

Authors:  Gregory R Boyce; Stephen N Greszler; Jeffrey S Johnson; Xin Linghu; Justin T Malinowski; David A Nicewicz; Andrew D Satterfield; Daniel C Schmitt; Kimberly M Steward
Journal:  J Org Chem       Date:  2012-03-23       Impact factor: 4.354

9.  Catalytic asymmetric α-acylation of tertiary amines mediated by a dual catalysis mode: N-heterocyclic carbene and photoredox catalysis.

Authors:  Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-05-02       Impact factor: 15.419

10.  Enantioselective synthesis of alpha,alpha-disubstituted cyclopentenes by an N-heterocyclic carbene-catalyzed desymmetrization of 1,3-diketones.

Authors:  Manabu Wadamoto; Eric M Phillips; Troy E Reynolds; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-07-31       Impact factor: 15.419
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