Literature DB >> 22087753

The decarboxylative Strecker reaction.

Deepankar Das1, Matthew T Richers, Longle Ma, Daniel Seidel.   

Abstract

α-Amino acids react with aldehydes in the presence of a cyanide source to form α-amino nitriles in what can be considered a decarboxylative variant of the classical Strecker reaction. This unprecedented transformation does not require the use of a metal catalyst and provides facile access to valuable α-amino nitriles that are inaccessible by traditional Strecker chemistry.

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Year:  2011        PMID: 22087753     DOI: 10.1021/ol202957d

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


  17 in total

1.  Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

Authors:  Matthew T Richers; Indubhusan Deb; Alena Yu Platonova; Chen Zhang; Daniel Seidel
Journal:  Synthesis (Stuttg)       Date:  2013-10-06       Impact factor: 3.157

2.  An Ugi Reaction Incorporating a Redox-Neutral Amine C-H Functionalization Step.

Authors:  Zhengbo Zhu; Daniel Seidel
Journal:  Org Lett       Date:  2016-01-19       Impact factor: 6.005

3.  Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.

Authors:  Deepankar Das; Daniel Seidel
Journal:  Org Lett       Date:  2013-08-19       Impact factor: 6.005

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

Authors:  Anirudra Paul; N R Thimmegowda; Thiago Galani Cruz; Daniel Seidel
Journal:  Org Lett       Date:  2018-01-12       Impact factor: 6.005

5.  Condensation-Based Methods for the C-H Bond Functionalization of Amines.

Authors:  Weijie Chen; Daniel Seidel
Journal:  Synthesis (Stuttg)       Date:  2021-09-02       Impact factor: 3.157

Review 6.  1,3-Dipolar cycloaddition reactions of isatin-derived azomethine ylides for the synthesis of spirooxindole and indole-derived scaffolds: recent developments.

Authors:  Fatemeh Rostami Miankooshki; Mohammad Bayat; Shima Nasri; Narges Habibi Samet
Journal:  Mol Divers       Date:  2022-08-04       Impact factor: 3.364

7.  Redox-neutral copper(II) carboxylate catalyzed α-alkynylation of amines.

Authors:  Deepankar Das; Aaron X Sun; Daniel Seidel
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-25       Impact factor: 15.336

8.  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

9.  Metal-free α-amination of secondary amines: computational and experimental evidence for azaquinone methide and azomethine ylide intermediates.

Authors:  Arne Dieckmann; Matthew T Richers; Alena Yu Platonova; Chen Zhang; Daniel Seidel; K N Houk
Journal:  J Org Chem       Date:  2013-04-02       Impact factor: 4.354

10.  Dual C-H functionalization of N-aryl amines: synthesis of polycyclic amines via an oxidative Povarov approach.

Authors:  Chang Min; Abbas Sanchawala; Daniel Seidel
Journal:  Org Lett       Date:  2014-05-01       Impact factor: 6.005

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