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Literature DB >> 24501432

Synthesis of Cyclic α-Aminophosphonates through Copper Catalyzed Enamine Activation.

Junbin Han¹, Robert S Paton², Bo Xu¹, Gerald B Hammond¹.

Abstract

A copper-catalyzed tandem cyclization triggered addition strategy that relies on electrophilic enamine activation has been used to synthesize various cyclic α-aminophosphonates derivatives in good to excellent yields. Both five and six membered rings can be generated under mild conditions with high regioselectivity. A mechanism based on copper catalyzed enamine activation is proposed.

Entities: CellLine Chemical Disease Gene

Keywords: copper; cyclic α-aminophosphonates; cyclization; enamine; hydroamination

Year: 2013 PMID： 24501432 PMCID： PMC3910425 DOI： 10.1055/s-0032-1317984

Source DB: PubMed Journal: Synthesis (Stuttg) ISSN： 0039-7881 Impact factor: 3.157

25 in total

1. Enantioselective synthesis of propargylamines by copper-catalyzed addition of alkynes to enamines.

Authors: Christopher Koradin; Kurt Polborn; Paul Knochel
Journal: Angew Chem Int Ed Engl Date: 2002-07-15 Impact factor: 15.336

Review 2. Fluorinated phosphonates: synthesis and biomedical application.

Authors: Vadim D Romanenko; Valery P Kukhar
Journal: Chem Rev Date: 2006-09 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. Hydroamination: direct addition of amines to alkenes and alkynes.

Authors: Thomas E Müller; Kai C Hultzsch; Miguel Yus; Francisco Foubelo; Mizuki Tada
Journal: Chem Rev Date: 2008-08-26 Impact factor: 60.622

5. Organocatalytic approach to benzofused nitrogen-containing heterocycles: enantioselective total synthesis of (+)-angustureine.

Authors: Santos Fustero; Javier Moscardó; Diego Jiménez; María Dolores Pérez-Carrión; María Sánchez-Roselló; Carlos Del Pozo
Journal: Chemistry Date: 2008 Impact factor: 5.236

6. Copper-catalyzed aerobic phosphonation of sp3 C-H bonds.

Authors: Olivier Baslé; Chao-Jun Li
Journal: Chem Commun (Camb) Date: 2009-06-05 Impact factor: 6.222

7. Diversity-oriented synthesis of dibenzoazocines and dibenzoazepines via a microwave-assisted intramolecular A(3)-coupling reaction.

Authors: Jitender B Bariwal; Denis S Ermolat'ev; Toma N Glasnov; Kristof Van Hecke; Vaibhav P Mehta; Luc Van Meervelt; C Oliver Kappe; Erik V Van der Eycken
Journal: Org Lett Date: 2010-06-18 Impact factor: 6.005

8. Copper/DIPEA-catalyzed, aldehyde-induced tandem decarboxylation-coupling of natural α-amino acids and phosphites or secondary phosphine oxides.

Authors: Dongxu Yang; Depeng Zhao; Lijuan Mao; Linqing Wang; Rui Wang
Journal: J Org Chem Date: 2011-07-06 Impact factor: 4.354

Synthesis of Cyclic α-Aminophosphonates through Copper Catalyzed Enamine Activation.

1. Enantioselective synthesis of propargylamines by copper-catalyzed addition of alkynes to enamines.

Review 2. Fluorinated phosphonates: synthesis and biomedical application.

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

Review 4. Hydroamination: direct addition of amines to alkenes and alkynes.

5. Organocatalytic approach to benzofused nitrogen-containing heterocycles: enantioselective total synthesis of (+)-angustureine.

6. Copper-catalyzed aerobic phosphonation of sp3 C-H bonds.

7. Diversity-oriented synthesis of dibenzoazocines and dibenzoazepines via a microwave-assisted intramolecular A(3)-coupling reaction.

8. Copper/DIPEA-catalyzed, aldehyde-induced tandem decarboxylation-coupling of natural α-amino acids and phosphites or secondary phosphine oxides.

9. A versatile annulation protocol toward novel constrained phosphinic peptidomimetics.

10. Phosphatase inhibitors--III. Benzylaminophosphonic acids as potent inhibitors of human prostatic acid phosphatase.

1. Synthesis of Pyrrolidines and Pyrroles via Tandem Amination/Cyanation/Alkylation and Amination/Oxidation Sequences.

Review 2. Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates.