Literature DB >> 23398467

Unstabilized azomethine ylides for the stereoselective synthesis of substituted piperidines, tropanes, and azabicyclo[3.1.0] systems.

Michael A Ischay1, Michael K Takase, Robert G Bergman, Jonathan A Ellman.   

Abstract

Acid treatment of densely substituted 2-silyl-1,2-dihydropyridines provides a new and convenient entry to reactive azomethine ylides that can (1) be protonated and reduced with high stereoselectivity to give piperidines, (2) participate in [3 + 2] dipolar cycloaddition to give tropanes, and (3) undergo a Nazarov-like 6-π electrocyclization that upon reduction give 2-azabicyclo[3.1.0] systems.

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Year:  2013        PMID： 23398467      PMCID： PMC3586708          DOI： 10.1021/ja312311k

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


  43 in total

1.  Organometallic enantiomeric scaffolding: a strategy for the enantiocontrolled construction of regio- and stereodivergent trisubstituted piperidines from a common precursor.

Authors:  Heilam Wong; Ethel C Garnier-Amblard; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2011-04-22       Impact factor: 15.419

2.  Intramolecular dipolar cycloaddition reactions of azomethine ylides.

Authors:  Iain Coldham; Richard Hufton
Journal:  Chem Rev       Date:  2005-07       Impact factor: 60.622

3.  Construction of enantiopure pyrrolidine ring system via asymmetric [3+2]-cycloaddition of azomethine ylides.

Authors:  Ganesh Pandey; Prabal Banerjee; Smita R Gadre
Journal:  Chem Rev       Date:  2006-11       Impact factor: 60.622

4.  Synthesis of pyrrolo-isoquinolines related to the lamellarins using silver-catalyzed cycloisomerization/dipolar cycloaddition.

Authors:  Shun Su; John A Porco
Journal:  J Am Chem Soc       Date:  2007-06-01       Impact factor: 15.419

5.  Oxidative coupling of aromatic substrates with alkynes and alkenes under rhodium catalysis.

Authors:  Tetsuya Satoh; Masahiro Miura
Journal:  Chemistry       Date:  2010-10-04       Impact factor: 5.236

Review 6.  Towards mild metal-catalyzed C-H bond activation.

Authors:  Joanna Wencel-Delord; Thomas Dröge; Fan Liu; Frank Glorius
Journal:  Chem Soc Rev       Date:  2011-06-10       Impact factor: 54.564

7.  Cascade cyclization, dipolar cycloaddition to bridged tricyclic amines related to the Daphniphyllum alkaloids.

Authors:  Iain Coldham; Adam J M Burrell; Hélène D S Guerrand; Niall Oram
Journal:  Org Lett       Date:  2011-02-11       Impact factor: 6.005

Review 8.  C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals.

Authors:  Junichiro Yamaguchi; Atsushi D Yamaguchi; Kenichiro Itami
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-06       Impact factor: 15.336

9.  Chiral cyclopentadienyl ligands as stereocontrolling element in asymmetric C-H functionalization.

Authors:  Baihua Ye; Nicolai Cramer
Journal:  Science       Date:  2012-10-26       Impact factor: 47.728

10.  Synthesis of alkaloid (-)-205B via stereoselective reductive cross-coupling and intramolecular [3+2] cycloaddition.

Authors:  Dexi Yang; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2012-09-07       Impact factor: 15.419
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  10 in total

1.  New Regio- and Stereoselective Cascades via Unstabilized Azomethine Ylide Cycloadditions for the Synthesis of Highly Substituted Tropane and Indolizidine Frameworks.

Authors:  Shuming Chen; Vlad Bacauanu; Tobias Knecht; Brandon Q Mercado; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2016-09-19       Impact factor: 15.419

2.  Regio- and stereoselective 1,2-dihydropyridine alkylation/addition sequence for the synthesis of piperidines with quaternary centers.

Authors:  Simon Duttwyler; Shuming Chen; Colin Lu; Brandon Q Mercado; Robert G Bergman; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-06       Impact factor: 15.336

3.  Formation of Aminocyclopentadienes from Silyldihydropyridines: Ring Contractions Driven by Anion Stabilization.

Authors:  Morgan M Walker; Shuming Chen; Brandon Q Mercado; K N Houk; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2018-04-26       Impact factor: 15.336

4.  Regio- and Diastereoselective Synthesis of Highly Substituted, Oxygenated Piperidines from Tetrahydropyridines.

Authors:  Shuming Chen; Brandon Q Mercado; Robert G Bergman; Jonathan A Ellman
Journal:  J Org Chem       Date:  2015-06-22       Impact factor: 4.354

5.  Synthesis of ent-ketorfanol via a C-H alkenylation/torquoselective 6π electrocyclization cascade.

Authors:  Eric M Phillips; Tehetena Mesganaw; Ashay Patel; Simon Duttwyler; Brandon Q Mercado; Kendall N Houk; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-17       Impact factor: 15.336

6.  Catalytic Kinetic Resolution of Disubstituted Piperidines by Enantioselective Acylation: Synthetic Utility and Mechanistic Insights.

Authors:  Benedikt Wanner; Imants Kreituss; Osvaldo Gutierrez; Marisa C Kozlowski; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2015-08-26       Impact factor: 15.419

7.  Rh(I)-Catalyzed Cycloisomerization of 1,6-Enynes.

Authors:  Yuji Matsushima; Eric M Phillips; Robert G Bergman; Jonathan A Ellman
Journal:  Synlett       Date:  2015-02-27       Impact factor: 2.454

Review 8.  Rhodium-Catalyzed C-H Alkenylation/Electrocyclization Cascade Provides Dihydropyridines That Serve as Versatile Intermediates to Diverse Nitrogen Heterocycles.

Authors:  Sun Dongbang; Danielle N Confair; Jonathan A Ellman
Journal:  Acc Chem Res       Date:  2021-03-19       Impact factor: 22.384

Review 9.  Preparative Synthesis of Highly Substituted Tetrahydropyridines via a Rh(I)-Catalyzed C-H Functionalization Sequence.

Authors:  Tehetena Mesganaw; Jonathan A Ellman
Journal:  Org Process Res Dev       Date:  2014-08-29       Impact factor: 3.317

Review 10.  Convergent Synthesis of Diverse Tetrahydropyridines via Rh(I)-Catalyzed C-H Functionalization Sequences.

Authors:  Tehetena Mesganaw; Jonathan A Ellman
Journal:  Org Process Res Dev       Date:  2014-08-29       Impact factor: 3.317
  10 in total

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