Literature DB >> 20055374

Aldehyde- and ketone-induced tandem decarboxylation-coupling (Csp(3)-Csp) of natural alpha-amino acids and alkynes.

Hai-Peng Bi1, Qingfeng Teng, Min Guan, Wen-Wen Chen, Yong-Min Liang, Xiaojun Yao, Chao-Jun Li.   

Abstract

An interesting aldehyde- and ketone-induced intermolecular tandem decarboxylation-coupling (Csp(3)-Csp) catalyzed by copper with use of natural alpha-amino acids as starting materials is developed under neutral conditions with the production of CO(2) and H(2)O as the only byproducts. Various functionalized nitrogen-containing compounds were obtained by this method. In these processes, interesting regioselectivites of the alkylation were observed, which has been rationalized by the relative stability of proposed resonance structures based on computation methods.

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Year:  2010        PMID: 20055374     DOI: 10.1021/jo902319h

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


  17 in total

1.  Decarboxylative Alkynylation.

Authors:  Joel M Smith; Tian Qin; Rohan R Merchant; Jacob T Edwards; Lara R Malins; Zhiqing Liu; Guanda Che; Zichao Shen; Scott A Shaw; Martin D Eastgate; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-01       Impact factor: 15.336

2.  The Redox-A3 Reaction.

Authors:  Daniel Seidel
Journal:  Org Chem Front       Date:  2014-06-01       Impact factor: 5.281

3.  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

4.  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

5.  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

6.  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

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.  Merging photoredox and nickel catalysis: decarboxylative cross-coupling of carboxylic acids with vinyl halides.

Authors:  Adam Noble; Stefan J McCarver; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2015-01-12       Impact factor: 15.419

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