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Literature DB >> 20394364

Tandem processes identified from reaction screening: nucleophilic addition to aryl N-phosphinylimines employing La(III)-TFAA activation.

Hidenori Kinoshita¹, Oscar J Ingham, Winnie W Ong, Aaron B Beeler, John A Porco.

Abstract

Reaction screening of nucleophilic reaction partners for addition to N-diphenylphosphinylimines employing lanthanum(III) triflate as a catalyst and trifluoroacetic anhydride (TFAA) as an activator is reported. A number of tandem processes leading to novel chemotypes including aza-Prins/intramolecular Friedel-Crafts annulations have been identified, and both reaction scope and mechanism further investigated.

Entities: Chemical

Mesh：

Substances：

Year: 2010 PMID： 20394364 PMCID： PMC2881420 DOI： 10.1021/ja100346w

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

24 in total

1. Synthesis and structure revision of calyxin natural products.

Authors: Xia Tian; James J Jaber; Scott D Rychnovsky
Journal: J Org Chem Date: 2006-04-14 Impact factor: 4.354

2. Synthetic studies in the intramolecular carbocyclization of N-acyloxyiminium ions. Stereoelectronic and steric implications of nucleophilic alkene, alkyne, and allene tethers.

Authors: Stephen Hanessian; Martin Tremblay; Mauro Marzi; Juan R Del Valle
Journal: J Org Chem Date: 2005-06-24 Impact factor: 4.354

3. Enantioselective synthesis of (+)-cortistatin a, a potent and selective inhibitor of endothelial cell proliferation.

Authors: Hong Myung Lee; Cristina Nieto-Oberhuber; Matthew D Shair
Journal: J Am Chem Soc Date: 2008-12-17 Impact factor: 15.419

4. Total synthesis of diverse carbogenic complexity within the resveratrol class from a common building block.

Authors: Scott A Snyder; Steven P Breazzano; Audrey G Ross; Yunqing Lin; Alexandros L Zografos
Journal: J Am Chem Soc Date: 2009-02-11 Impact factor: 15.419

5. A copper(II)-catalyzed aza-Friedel-Crafts reaction of N-(2-pyridyl)sulfonyl aldimines: synthesis of unsymmetrical diaryl amines and triaryl methanes.

Authors: Jorge Esquivias; Ramón Gómez Arrayás; Juan C Carretero
Journal: Angew Chem Int Ed Engl Date: 2006-01-16 Impact factor: 15.336

Review 6. Exploration of fundamental and synthetic aspects of the intramolecular 4 + 3 cycloaddition reaction.

Authors: M Harmata
Journal: Acc Chem Res Date: 2001-07 Impact factor: 22.384

7. Development of a Friedel-Crafts triflation.

Authors: Marc A Grundl; Anne Kaster; Ellen D Beaulieu; Dirk Trauner
Journal: Org Lett Date: 2006-11-23 Impact factor: 6.005

8. Catalytic, enantioselective alkylation of alpha-imino esters: the synthesis of nonnatural alpha-amino acid derivatives.

Authors: Dana Ferraris; Brandon Young; Christopher Cox; Travis Dudding; William J Drury; Lev Ryzhkov; Andrew E Taggi; Thomas Lectka
Journal: J Am Chem Soc Date: 2002-01-09 Impact factor: 15.419

9. The N-acyloxyiminium ion aza-Prins route to octahydroindoles: total synthesis and structural confirmation of the antithrombotic marine natural product oscillarin.

Authors: Stephen Hanessian; Martin Tremblay; Jens F W Petersen
Journal: J Am Chem Soc Date: 2004-05-19 Impact factor: 15.419

10. Optically active aromatic and heteroaromatic alpha-amino acids by a one-pot catalytic enantioselective addition of aromatic and heteroaromatic C-H bonds to alpha-imino esters.

Authors: Steen Saaby; Pau Bayón; Pompiliu S Aburel; Karl Anker Jørgensen
Journal: J Org Chem Date: 2002-06-14 Impact factor: 4.354

7 in total

7. Catalytic [2 + 2 + 2] cycloaddition with indium(iii)-activated formaldimines: a practical and selective access to hexahydropyrimidines and 1,3-diamines from alkenes.

Authors: Hui Zhou; Hetti Handi Chaminda Lakmal; Jonathan M Baine; Henry U Valle; Xue Xu; Xin Cui
Journal: Chem Sci Date: 2017-07-24 Impact factor: 9.825

7 in total

Tandem processes identified from reaction screening: nucleophilic addition to aryl N-phosphinylimines employing La(III)-TFAA activation.

1. Synthesis and structure revision of calyxin natural products.

2. Synthetic studies in the intramolecular carbocyclization of N-acyloxyiminium ions. Stereoelectronic and steric implications of nucleophilic alkene, alkyne, and allene tethers.

3. Enantioselective synthesis of (+)-cortistatin a, a potent and selective inhibitor of endothelial cell proliferation.

4. Total synthesis of diverse carbogenic complexity within the resveratrol class from a common building block.

5. A copper(II)-catalyzed aza-Friedel-Crafts reaction of N-(2-pyridyl)sulfonyl aldimines: synthesis of unsymmetrical diaryl amines and triaryl methanes.

Review 6. Exploration of fundamental and synthetic aspects of the intramolecular 4 + 3 cycloaddition reaction.

7. Development of a Friedel-Crafts triflation.

8. Catalytic, enantioselective alkylation of alpha-imino esters: the synthesis of nonnatural alpha-amino acid derivatives.

9. The N-acyloxyiminium ion aza-Prins route to octahydroindoles: total synthesis and structural confirmation of the antithrombotic marine natural product oscillarin.

10. Optically active aromatic and heteroaromatic alpha-amino acids by a one-pot catalytic enantioselective addition of aromatic and heteroaromatic C-H bonds to alpha-imino esters.

1. Synthesis and reactivity of bicyclo[3.2.1]octanoid-derived cyclopropanes.

Review 2. Contemporary screening approaches to reaction discovery and development.

3. Multidimensional Screening and Methodology Development for Condensations Involving Complex 1,2-Diketones.

4. A simple, multidimensional approach to high-throughput discovery of catalytic reactions.

5. Synthesis of a novel chemotype via sequential metal-catalyzed cycloisomerizations.

6. Identifying lead hits in catalyst discovery by screening and deconvoluting complex mixtures of catalyst components.

7. Catalytic [2 + 2 + 2] cycloaddition with indium(iii)-activated formaldimines: a practical and selective access to hexahydropyrimidines and 1,3-diamines from alkenes.