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Literature DB >> 21718035

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

Dongxu Yang¹, Depeng Zhao, Lijuan Mao, Linqing Wang, Rui Wang.

Abstract

A copper/DIPEA-catalyzed, aldehyde-induced intermolecular decarboxylative coupling reaction of natural α-amino acids and phosphites or secondary phosphine oxides was developed. In this process, a series of potentially useful ligands for organic synthesis and biologically important unnatural amino acid derivatives (tertiary amino phosphorus compounds) were obtained.

Entities: Chemical

Mesh：

Substances：

Year: 2011 PMID： 21718035 DOI： 10.1021/jo200981h

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

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Cited

16 in total

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

Authors: Junbin Han; Robert S Paton; Bo Xu; Gerald B Hammond
Journal: Synthesis (Stuttg) Date: 2013-02-01 Impact factor: 3.157

2. 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

Review 9. The azomethine ylide route to amine C-H functionalization: redox-versions of classic reactions and a pathway to new transformations.

Authors: Daniel Seidel
Journal: Acc Chem Res Date: 2015-01-06 Impact factor: 22.384

10. Decarboxylative Annulation of α-Amino Acids with γ-Nitroaldehydes.

Authors: YoungKu Kang; Daniel Seidel
Journal: Org Lett Date: 2016-08-10 Impact factor: 6.005

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

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

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

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

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

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

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

Review 7. Decarboxylative cross-coupling reactions for P(O)-C bond formation.

8. Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates.

Review 9. The azomethine ylide route to amine C-H functionalization: redox-versions of classic reactions and a pathway to new transformations.

10. Decarboxylative Annulation of α-Amino Acids with γ-Nitroaldehydes.