Mechanistic insights for the transprotection of tertiary amines with Boc2O via charged carbamates: access to both enantiomers of 2-azanorbornane-3-exo-carboxylic acids-Reference-Cited by-同舟云学术

Mechanistic insights for the transprotection of tertiary amines with Boc2O via charged carbamates: access to both enantiomers of 2-azanorbornane-3-exo-carboxylic acids

Published:2019 Issue:20 Volume:6 Page:3540-3554
ISSN:2052-4129
Container-title:Organic Chemistry Frontiers
language:en
Short-container-title:Org. Chem. Front.

Author:

Sampaio-Dias Ivo E.¹²³⁴⁵^ORCID,Silva-Reis Sara C.¹²³⁴⁵^ORCID,Pinto da Silva Luís⁶²⁷⁵⁸^ORCID,García-Mera Xerardo⁹¹⁰¹¹¹²¹³^ORCID,Maestro Miguel A.¹⁴³¹⁵¹⁶¹³^ORCID,Rodríguez-Borges José E.¹²³⁴⁵^ORCID

Affiliation:

1. LAQV/REQUIMTE

2. Department of Chemistry and Biochemistry

3. Faculty of Sciences

4. University of Porto

5. 4169-007 Porto

6. Chemistry Research Unit (CIQUP)

7. Faculty of Sciences of University of Porto

8. Portugal

9. Department of Organic Chemistry

10. Faculty of Pharmacy

11. University of Santiago de Compostela

12. Santiago de Compostela

13. Spain

14. Department of Chemistry-CICA

15. University of Coruña

16. A Coruña

Abstract

Development of a synthetic methodology for the selective transprotection in hindered tertiary amines using Boc₂O under N–C hydrogenolysis catalyzed by Pd/C: access to both enantiomers of 2-azanorbornane-3-exo-carboxylates.

Funder

Fundação para a Ciência e a Tecnologia

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2019/QO/C9QO00957D

Reference80 articles.

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2. Asymmetric Synthesis of (S,S,S)-2-Aza-bicyclo-[3.3.0]-octane-3-carboxylic Acid Benzyl Ester: Formal Synthesis of Ramipril

3. An improved synthesis of enantiopure 2-azabicyclo[2.2.1]heptane-3-carboxylic acid

4. Novel l-prolyl-l-leucylglycinamide (PLG) tripeptidomimetics based on a 2-azanorbornane scaffold as positive allosteric modulators of the D2R

5. Synthesis and evaluation of chiral bicyclic proline FKBP12 ligands

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