Literature DB >> 16881615

Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives.

Erin C Burger1, Jon A Tunge.   

Abstract

Protected homoallylic amines are synthesized by the decarboxylative coupling of alpha-amino acid derivatives. The catalytic C-C bond-forming reaction relies on the bioinspired decarboxylative metalation of alpha-amino acids to produce alpha-amino anion equivalents. The alpha-amino anion equivalents are intercepted by pi-allyl palladium electrophiles to produce substituted homoallylic amines.

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Year:  2006        PMID: 16881615     DOI: 10.1021/ja063115x

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  20 in total

1.  Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Authors:  Minyan Li; Baris Yücel; Javier Adrio; Ana Bellomo; Patrick J Walsh
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

2.  Deacylative allylation: allylic alkylation via retro-Claisen activation.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2011-08-24       Impact factor: 15.419

3.  Umpolung Synthesis of Diarylmethylamines via Palladium-Catalyzed Arylation of N-Benzyl Aldimines.

Authors:  Minyan Li; Baris Yucel; Jacqueline Jiménez; Madeline Rotella; Yue Fu; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2016-05-12       Impact factor: 5.837

Review 4.  Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors:  Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
Journal:  Chem Rev       Date:  2011-01-14       Impact factor: 60.622

5.  Homologation of α-aryl amino acids through quinone-catalyzed decarboxylation/Mukaiyama-Mannich addition.

Authors:  Benjamin J Haugeberg; Johnny H Phan; Xinyun Liu; Thomas J O'Connor; Michael D Clift
Journal:  Chem Commun (Camb)       Date:  2017-03-09       Impact factor: 6.222

6.  Palladium-catalyzed C(sp(3))-H Arylation of N-Boc benzylalkylamines via a deprotonative cross-coupling process.

Authors:  Nusrah Hussain; Byeong-Seon Kim; Patrick J Walsh
Journal:  Chemistry       Date:  2015-06-30       Impact factor: 5.236

7.  Rapid decarboxylative allylation of nitroalkanes.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  Org Lett       Date:  2010-02-19       Impact factor: 6.005

8.  Decarboxylative allylation using sulfones as surrogates of alkanes.

Authors:  Jimmie D Weaver; Jon A Tunge
Journal:  Org Lett       Date:  2008-09-12       Impact factor: 6.005

9.  Regiospecific decarboxylative allylation of nitriles.

Authors:  Antonio Recio; Jon A Tunge
Journal:  Org Lett       Date:  2009-12-17       Impact factor: 6.005

10.  Ruthenium catalyzed decarbonylative arylation at sp3 carbon centers in pyrrolidine and piperidine heterocycles.

Authors:  Denis V Gribkov; Stefan J Pastine; Michael Schnürch; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2007-09-06       Impact factor: 15.419

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