Literature DB >> 24604837

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

Simon Duttwyler1, Shuming Chen, Colin Lu, Brandon Q Mercado, Robert G Bergman, Jonathan A Ellman.   

Abstract

The first example of C alkylation of 1,2-dihydropyridines with alkyl triflates and Michael acceptors was developed to introduce quaternary carbon centers with high regio- and diastereoselectivity. Hydride or carbon nucleophile addition to the resultant iminium ion also proceeded with high diastereoselectivity. Carbon nucleophile addition results in an unprecedented level of substitution to provide piperidine rings with adjacent tetrasubstituted carbon atoms.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkylation; diastereoselectivity; heterocycles; reduction; synthetic methods

Mesh：

Substances：

Year:  2014        PMID： 24604837      PMCID： PMC4058641          DOI： 10.1002/anie.201310517

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  25 in total

Review 1.  The chemistry and pharmacology of tetrahydropyridines.

Authors:  N N Mateeva; L L Winfield; K K Redda
Journal:  Curr Med Chem       Date:  2005       Impact factor: 4.530

2.  [4 + 2] Cyclocondensation reactions of tungsten-dihydropyridine complexes and the generation of tri- and tetrasubstituted piperidines.

Authors:  Daniel P Harrison; Diana A Iovan; William H Myers; Michal Sabat; Sisi Wang; Victor E Zottig; W Dean Harman
Journal:  J Am Chem Soc       Date:  2011-10-26       Impact factor: 15.419

3.  Synthesis of quaternary α-methyl α-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine.

Authors:  Cedric L Hugelshofer; Kevin T Mellem; Andrew G Myers
Journal:  Org Lett       Date:  2013-06-07       Impact factor: 6.005

4.  Grob fragmentation of 2-azabicyclo[2.2.2]oct-7-ene: tool for the stereoselective synthesis of polysubstituted piperidines.

Authors:  Gérald Lemonnier; André B Charette
Journal:  J Org Chem       Date:  2012-06-15       Impact factor: 4.354

5.  Annulation of α,β-unsaturated imines and alkynes via cobalt-catalyzed olefinic C-H activation.

Authors:  Takeshi Yamakawa; Naohiko Yoshikai
Journal:  Org Lett       Date:  2012-12-21       Impact factor: 6.005

6.  Highly enantioselective rhodium-catalyzed [2+2+2] cycloaddition of diynes to sulfonimines.

Authors:  Muriel Amatore; David Lebœuf; Max Malacria; Vincent Gandon; Corinne Aubert
Journal:  J Am Chem Soc       Date:  2013-03-13       Impact factor: 15.419

7.  Escape from flatland: increasing saturation as an approach to improving clinical success.

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

Authors:  Michael A Ischay; Michael K Takase; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2013-02-11       Impact factor: 15.419

9.  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

Review 10.  Indolizidine and quinolizidine alkaloids.

Authors:  Joseph P Michael
Journal:  Nat Prod Rep       Date:  2007-12-13       Impact factor: 13.423
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  12 in total

1.  π-Facial Selectivities in Hydride Reductions of Hindered Endocyclic Iminium Ions.

Authors:  Shuming Chen; Amy Y Chan; Morgan M Walker; Jonathan A Ellman; K N Houk
Journal:  J Org Chem       Date:  2018-12-19       Impact factor: 4.354

2.  Atom-efficient regioselective 1,2-dearomatization of functionalized pyridines by an earth-abundant organolanthanide catalyst.

Authors:  Alexander S Dudnik; Victoria L Weidner; Alessandro Motta; Massimiliano Delferro; Tobin J Marks
Journal:  Nat Chem       Date:  2014-10-19       Impact factor: 24.427

3.  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

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.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622

Review 9.  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 10.  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
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