Literature DB >> 18529081

Improved protocol for asymmetric, intramolecular heteroatom Michael addition using organocatalysis: enantioselective syntheses of homoproline, pelletierine, and homopipecolic acid.

Erik C Carlson1, Lauren K Rathbone, Hua Yang, Nathan D Collett, Rich G Carter.   

Abstract

An improved protocol for the construction of enantioenriched pyrrolidine, indoline, and piperidine rings using an organocatalyzed, intramolecular heteroatom Michael addition is described. Application to the enantioselective synthesis of homoproline, homopipecolic acid, and pelletierine has been accomplished.

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Year:  2008        PMID： 18529081      PMCID： PMC2474690          DOI： 10.1021/jo800749t

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  23 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

2.  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

3.  Gold(I)-catalyzed intramolecular hydroamination of alkenyl carbamates.

Authors:  Xiaoqing Han; Ross A Widenhoefer
Journal:  Angew Chem Int Ed Engl       Date:  2006-03-03       Impact factor: 15.336

4.  Endomorphin-1 analogues containing beta-proline are mu-opioid receptor agonists and display enhanced enzymatic hydrolysis resistance.

Authors:  Giuliana Cardillo; Luca Gentilucci; Ahmed R Qasem; Fabio Sgarzi; Santi Spampinato
Journal:  J Med Chem       Date:  2002-06-06       Impact factor: 7.446

5.  Highly enantioselective conjugate additions to alpha,beta-unsaturated ketones catalyzed by a (salen)Al complex.

Authors:  Mark S Taylor; David N Zalatan; Andreas M Lerchner; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2005-02-02       Impact factor: 15.419

6.  Organocatalytic asymmetric 5-hydroxyisoxazolidine synthesis: a highly enantioselective route to beta-amino acids.

Authors:  Ismail Ibrahem; Ramon Rios; Jan Vesely; Gui-Ling Zhao; Armando Córdova
Journal:  Chem Commun (Camb)       Date:  2006-11-23       Impact factor: 6.222

7.  Chiral Diphenylprolinol TES ether promoted conjugate addition-aldol-dehydration reactions between alpha,beta-unsaturated aldehydes and 2-N-protected amino benzaldehydes.

Authors:  Hao Li; Jian Wang; Hexin Xie; Liansuo Zu; Wei Jiang; Eileen N Duesler; Wei Wang
Journal:  Org Lett       Date:  2007-02-14       Impact factor: 6.005

8.  Synthesis of cyclic and acyclic beta-amino acids via chelation-controlled 1,3-dipolar cycloaddition.

Authors:  Roger Hanselmann; Jiacheng Zhou; Philip Ma; Pat N Confalone
Journal:  J Org Chem       Date:  2003-10-31       Impact factor: 4.354

9.  Organocatalytic enantioselective [3+2] cycloaddition of azomethine ylides and alpha,beta-unsaturated aldehydes.

Authors:  Jose L Vicario; Silvia Reboredo; Dolores Badía; Luisa Carrillo
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

10.  Pd(II)-catalyzed enantioselective oxidative tandem cyclization reactions. Synthesis of indolines through C-N and C-C bond formation.

Authors:  Kai-Tai Yip; Min Yang; Ka-Lun Law; Nian-Yong Zhu; Dan Yang
Journal:  J Am Chem Soc       Date:  2006-03-15       Impact factor: 15.419
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  13 in total

1.  N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: a practical proline mimetic for facilitating enantioselective aldol reactions.

Authors:  Hua Yang; Rich G Carter
Journal:  Org Lett       Date:  2008-09-23       Impact factor: 6.005

2.  Enantioselective approach to quinolizidines: total synthesis of cermizine D and formal syntheses of senepodine G and cermizine C.

Authors:  Nagarathanam Veerasamy; Erik C Carlson; Nathan D Collett; Mrinmoy Saha; Rich G Carter
Journal:  J Org Chem       Date:  2013-04-29       Impact factor: 4.354

3.  Expedient enantioselective synthesis of cermizine D.

Authors:  Nagarathanam Veerasamy; Erik C Carlson; Rich G Carter
Journal:  Org Lett       Date:  2012-02-28       Impact factor: 6.005

4.  Triazole-containing isothiazolidine 1,1-dioxide library synthesis: one-pot, multi-component protocols for small molecular probe discovery.

Authors:  Alan Rolfe; Thomas O Painter; Naeem Asad; Moon Young Hur; Kyu Ok Jeon; Marek Brzozowski; Sarra V Klimberg; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Conrad Santini; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2011-08-25       Impact factor: 3.784

5.  Application of a Double Aza-Michael Reaction in a 'Click, Click, Cy-Click' Strategy: From Bench to Flow.

Authors:  Qin Zang; Salim Javed; Farman Ullah; Aihua Zhou; Christopher A Knudtson; Danse Bi; Fatima Z Basha; Michael G Organ; Paul R Hanson
Journal:  Synthesis (Stuttg)       Date:  2011-09-01       Impact factor: 3.157

6.  Stereoselective synthesis of the eastern quinolizidine portion of himeradine A.

Authors:  Nathan D Collett; Rich G Carter
Journal:  Org Lett       Date:  2011-07-12       Impact factor: 6.005

7.  Development of an enantioselective route toward the Lycopodium alkaloids: total synthesis of lycopodine.

Authors:  Hua Yang; Rich G Carter
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

8.  Highly stereoselective and scalable anti-aldol reactions using N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: scope and origins of stereoselectivities.

Authors:  Hua Yang; Subham Mahapatra; Paul Ha-Yeon Cheong; Rich G Carter
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

9.  Toward a unified approach for the lycopodines: synthesis of 10-hydroxylycopodine, deacetylpaniculine, and paniculine.

Authors:  Mrinmoy Saha; Rich G Carter
Journal:  Org Lett       Date:  2013-02-05       Impact factor: 6.005

10.  Mannich-type Reactions of Cyclic Nitrones: Effective Methods for the Enantioselective Synthesis of Piperidine-containing Alkaloids.

Authors:  Vladislav G Lisnyak; Tessa Lynch-Colameta; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-19       Impact factor: 15.336
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