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Literature DB >> 29328663

Decarboxylative Annulation of α-Amino Acids with β-Ketoaldehydes.

Anirudra Paul^1,2, N R Thimmegowda¹, Thiago Galani Cruz¹, Daniel Seidel^1,2.

Abstract

Indolizidine and quinolizidine derivatives are readily assembled from l-proline or (±)-pipecolic acid and β-ketoaldehydes via a decarboxylative annulation process. These reactions are promoted by acetic acid and involve azomethine ylides as reactive intermediates.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2018 PMID： 29328663 PMCID： PMC5937137 DOI： 10.1021/acs.orglett.7b03721

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

47 in total

1. Intramolecular dipolar cycloaddition reactions of azomethine ylides.

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

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. Alpha-amination of nitrogen heterocycles: ring-fused aminals.

Authors: Chen Zhang; Chandra Kanta De; Rudrajit Mal; Daniel Seidel
Journal: J Am Chem Soc Date: 2008-01-16 Impact factor: 15.419

Review 4. Decarboxylation as the Key Step in C-C Bond-Forming Reactions.

Authors: Tuhin Patra; Debabrata Maiti
Journal: Chemistry Date: 2017-02-14 Impact factor: 5.236

5. Regioselective Metal-Free Decarboxylative Multicomponent Coupling of α-Amino Acids, Aldehydes and Isonitriles Leading to N-Substituted Azacyclic-2-carboxamides with Antithrombotic Activity.

Authors: Shashikant U Dighe; Anil Kumar K S; Smriti Srivastava; Pankaj Shukla; Surendra Singh; Madhu Dikshit; Sanjay Batra
Journal: J Org Chem Date: 2014-11-26 Impact factor: 4.354

6. C-H functionalization of cyclic amines: redox-annulations with α,β-unsaturated carbonyl compounds.

Authors: YoungKu Kang; Matthew T Richers; Conrad H Sawicki; Daniel Seidel
Journal: Chem Commun (Camb) Date: 2015-07-07 Impact factor: 6.222

7. Cobalt-Catalyzed Decarboxylative Acetoxylation of Amino Acids and Arylacetic Acids.

Authors: Kun Xu; Zhiqiang Wang; Jinjin Zhang; Lintao Yu; Jiajing Tan
Journal: Org Lett Date: 2015-09-02 Impact factor: 6.005

8. Visible-Light-Induced Decarboxylative Functionalization of Carboxylic Acids and Their Derivatives.

Authors: Jun Xuan; Zhao-Guo Zhang; Wen-Jing Xiao
Journal: Angew Chem Int Ed Engl Date: 2015-10-28 Impact factor: 15.336

9. Nontraditional reactions of azomethine ylides: decarboxylative three-component couplings of alpha-amino acids.

Authors: Chen Zhang; Daniel Seidel
Journal: J Am Chem Soc Date: 2010-02-17 Impact factor: 15.419

10. Redox-Annulation of Cyclic Amines and β-Ketoaldehydes.

Authors: Weijie Chen; Daniel Seidel
Journal: Org Lett Date: 2016-02-19 Impact factor: 6.005

3 in total

1. Redox-Annulations of Cyclic Amines with ortho-Cyanomethylbenzaldehydes.

Authors: Anirudra Paul; Hemant S Chandak; Longle Ma; Daniel Seidel
Journal: Org Lett Date: 2020-01-27 Impact factor: 6.005

2. Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates.

Authors: Zhengbo Zhu; Hemant S Chandak; Daniel Seidel
Journal: Org Lett Date: 2018-06-25 Impact factor: 6.005

3. Traceless Redox-Annulations of Alicyclic Amines.

Authors: Dillon R L Rickertsen; Longle Ma; Anirudra Paul; Khalil A Abboud; Daniel Seidel
Journal: SynOpen Date: 2020-12-16

3 in total