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Literature DB >> 21174392

Application of catalytic dynamic resolution of N-Boc-2-lithiopiperidine to the asymmetric synthesis of 2-aryl and 2-vinyl piperidines.

Abstract

The highly enantioselective synthesis of 2-aryl- and 2-vinyl-piperidines has been accomplished through a catalytic dynamic resolution (CDR) of N-Boc-2-lithiopiperidine. The method has been applied to the synthesis of both enantiomers of the tobacco alkaloid anabasine.

Entities: Chemical Gene Species

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Year: 2010 PMID： 21174392 PMCID： PMC3031766 DOI： 10.1021/ol102682r

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

11 in total

1. Enantioselectivity in the reactions of chiral alpha-(N-carbamoyl)alkylcuprates.

Authors: R K Dieter; C M Topping; K R Chandupatla; K Lu
Journal: J Am Chem Soc Date: 2001-05-30 Impact factor: 15.419

Review 2. The combinatorial synthesis of bicyclic privileged structures or privileged substructures.

Authors: Douglas A Horton; Gregory T Bourne; Mark L Smythe
Journal: Chem Rev Date: 2003-03 Impact factor: 60.622

3. Enantioselective synthesis of 2-arylpiperidines from chiral lactams. A concise synthesis of (-)-anabasine.

Authors: Mercedes Amat; Margalida Cantó; Núria Llor; Joan Bosch
Journal: Chem Commun (Camb) Date: 2002-03-07 Impact factor: 6.222

4. Asymmetric substitutions of 2-lithiated N-boc-piperidine and N-Boc-azepine by dynamic resolution.

Authors: Iain Coldham; Sophie Raimbault; David T E Whittaker; Praful T Chovatia; Daniele Leonori; Jignesh J Patel; Nadeem S Sheikh
Journal: Chemistry Date: 2010-04-06 Impact factor: 5.236

5. Efficient enantiomeric synthesis of pyrrolidine and piperidine alkaloids from tobacco.

Authors: F X Felpin; S Girard; G Vo-Thanh; R J Robins; J Villiéras; J Lebreton
Journal: J Org Chem Date: 2001-09-21 Impact factor: 4.354

6. Asymmetric deprotonation of N-boc piperidine: react IR monitoring and mechanistic aspects.

Authors: Darren Stead; Giorgio Carbone; Peter O'Brien; Kevin R Campos; Iain Coldham; Adam Sanderson
Journal: J Am Chem Soc Date: 2010-06-02 Impact factor: 15.419

7. Highly enantioselective catalytic dynamic resolution of N-Boc-2-lithiopiperidine: synthesis of (R)-(+)-N-Boc-pipecolic acid, (S)-(-)-coniine, (S)-(+)-pelletierine, (+)-beta-conhydrine, and (S)-(-)-ropivacaine and formal synthesis of (-)-lasubine II and (+)-cermizine C.

Authors: Timothy K Beng; Robert E Gawley
Journal: J Am Chem Soc Date: 2010-09-08 Impact factor: 15.419

8. Synthesis of 2-arylpiperidines by palladium couplings of aryl bromides with organozinc species derived from deprotonation of N-boc-piperidine.

Authors: Iain Coldham; Daniele Leonori
Journal: Org Lett Date: 2008-08-07 Impact factor: 6.005

9. A readily-accessible (+)-sparteine surrogate.

Authors: Michael J Dearden; Catherine R Firkin; Jean-Paul R Hermet; Peter O'Brien
Journal: J Am Chem Soc Date: 2002-10-09 Impact factor: 15.419

10. Enantioselective Pd-catalyzed alpha-arylation of N-Boc-pyrrolidine: the key to an efficient and practical synthesis of a glucokinase activator.

Authors: Artis Klapars; Kevin R Campos; Jacob H Waldman; Daniel Zewge; Peter G Dormer; Cheng-yi Chen
Journal: J Org Chem Date: 2008-05-29 Impact factor: 4.354

16 in total

1. CATALYTIC DYNAMIC RESOLUTION APPLIED TO THE SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES: PREPARATION OF (+)-LUPETIDINE AND (-)-EPIDIHYDROPINIDINE.

Authors: Timothy K Beng; Robert E Gawley
Journal: Heterocycles Date: 2012-01-01 Impact factor: 0.831

Review 2. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors: Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal: Chem Rev Date: 2015-08-13 Impact factor: 60.622

3. Enantioselective Synthesis of α-(Hetero)aryl Piperidines through Asymmetric Hydrogenation of Pyridinium Salts and Its Mechanistic Insights.

Authors: Bo Qu; Hari P R Mangunuru; Sergei Tcyrulnikov; Daniel Rivalti; Olga V Zatolochnaya; Dmitry Kurouski; Suttipol Radomkit; Soumik Biswas; Shuklendu Karyakarte; Keith R Fandrick; Joshua D Sieber; Sonia Rodriguez; Jean-Nicolas Desrosiers; Nizar Haddad; Keith McKellop; Scott Pennino; Heewon Lee; Nathan K Yee; Jinhua J Song; Marisa C Kozlowski; Chris H Senanayake
Journal: Org Lett Date: 2018-02-20 Impact factor: 6.005

4. Asymmetric transition metal-catalyzed cross-coupling reactions for the construction of tertiary stereocenters.

Authors: Elizabeth C Swift; Elizabeth R Jarvo
Journal: Tetrahedron Date: 2013-07-22 Impact factor: 2.457

5. Synthetic applications and inversion dynamics of configurationally stable 2-lithio-2-arylpyrrolidines and -piperidines.

Authors: Timothy K Beng; Jin Sun Woo; Robert E Gawley
Journal: J Am Chem Soc Date: 2012-08-27 Impact factor: 15.419

6. α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp(3))-H Coupling.

Authors: Jillian E Spangler; Yoshihisa Kobayashi; Pritha Verma; Dong-Hui Wang; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2015-09-10 Impact factor: 15.419

7. Dynamics of catalytic resolution of 2-lithio-N-Boc-piperidine by ligand exchange.

Authors: Timothy K Beng; William S Tyree; Trent Parker; Chicheung Su; Paul G Williard; Robert E Gawley
Journal: J Am Chem Soc Date: 2012-09-25 Impact factor: 15.419

8. Functional-group-tolerant, nickel-catalyzed cross-coupling reaction for enantioselective construction of tertiary methyl-bearing stereocenters.

Authors: Hanna M Wisniewska; Elizabeth C Swift; Elizabeth R Jarvo
Journal: J Am Chem Soc Date: 2013-06-10 Impact factor: 15.419

9. Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters.

Authors: Chenlong Zhang; Weipeng Hu; Gabriel J Lovinger; Jing Jin; Jingjia Chen; James P Morken
Journal: J Am Chem Soc Date: 2021-08-23 Impact factor: 16.383

10. Configurationally Stable, Enantioenriched Organometallic Nucleophiles in Stereospecific Pd-Catalyzed Cross-Coupling Reactions: An Alternative Approach to Asymmetric Synthesis.

Authors: Chao-Yuan Wang; Joseph Derosaa; Mark R Biscoe
Journal: Chem Sci Date: 2015 Impact factor: 9.825