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Literature DB >> 16836413

Novel acetoxylation and C-C coupling reactions at unactivated positions in alpha-amino acid derivatives.

B V Subba Reddy¹, Leleti Rajender Reddy, E J Corey.

Abstract

[Structure: see text] Under special conditions, N-phthaloyl-alpha-amino acid amides of 8-aminoquinoline can be either acetoxylated or arylated selectively at the beta-carbon. In certain cases, arylation can be effected at the gamma-carbon.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 16836413 DOI： 10.1021/ol061389j

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

77 in total

1. Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

Authors: Tian-Sheng Mei; Lei Kou; Sandy Ma; Keary M Engle; Jin-Quan Yu
Journal: Synthesis (Stuttg) Date: 2012-05-25 Impact factor: 3.157

2. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors: Dmitry Shabashov; Olafs Daugulis
Journal: J Am Chem Soc Date: 2010-03-24 Impact factor: 15.419

3. Total synthesis and structural revision of the piperarborenines via sequential cyclobutane C-H arylation.

Authors: Will R Gutekunst; Phil S Baran
Journal: J Am Chem Soc Date: 2011-11-08 Impact factor: 15.419

4. Palladium-Catalyzed C-H Arylation Using Aryltrifluoroborates in Conjunction with a Mn^III Oxidant under Mild Conditions.

Authors: Cydney K Seigerman; Tiffiny M Micyus; Sharon R Neufeldt; Melanie S Sanford
Journal: Tetrahedron Date: 2013-07-08 Impact factor: 2.457

10. Synthetic and mechanistic studies of Pd-catalyzed C-H arylation with diaryliodonium salts: evidence for a bimetallic high oxidation state Pd intermediate.

Authors: Nicholas R Deprez; Melanie S Sanford
Journal: J Am Chem Soc Date: 2009-08-12 Impact factor: 15.419

Novel acetoxylation and C-C coupling reactions at unactivated positions in alpha-amino acid derivatives.

1. Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

2. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

3. Total synthesis and structural revision of the piperarborenines via sequential cyclobutane C-H arylation.

4. Palladium-Catalyzed C-H Arylation Using Aryltrifluoroborates in Conjunction with a Mn^III Oxidant under Mild Conditions.

5. Ligand-Enabled Arylation of γ-C-H Bonds.

6. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

7. Evolution of a Strategy for the Enantioselective Total Synthesis of (+)-Psiguadial B.

8. Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.

9. Iron-Catalyzed Oxyfunctionalization of Aliphatic Amines at Remote Benzylic C-H Sites.

10. Synthetic and mechanistic studies of Pd-catalyzed C-H arylation with diaryliodonium salts: evidence for a bimetallic high oxidation state Pd intermediate.