Progress and perspectives on directing group-assisted palladium-catalysed C–H functionalisation of amino acids and peptides

2021 ◽  
Author(s):  
Sadegh Shabani ◽  
Yuezhou Wu ◽  
Hannah G. Ryan ◽  
Craig A. Hutton
Keyword(s):  
Amino Acids ◽  
Directing Group

A review of Pd-assisted, directing-group mediated C–H functionalisation of amino acids and peptides.

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

scholarly journals Applications of tert-butanesulfinamide in the asymmetric synthesis of amines

2003 ◽  
Vol 75 (1) ◽  
pp. 39-46 ◽  
Author(s):  
J. A. Ellman
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Nucleophilic Addition ◽  
Amino Alcohols ◽  
Wide Range ◽  
Aldehydes And Ketones ◽  
Directing Group ◽  
High Yields ◽  
Direct Condensation

tert-Butanesulfinamide is prepared using catalytic enantioselective methods in two steps from the extremely inexpensive oil waste by-product, tert-butyl disulfide. Direct condensation of tert-butanesulfinamide with aldehydes and ketones provides tert-butanesulfinyl imines in uniformly high yields. The tert-butanesulfinyl group activates the imines for the addition of many different classes of nucleophiles, serves as a powerful chiral directing group, and after nucleophilic addition is readily cleaved by treatment with acid. A wide range of highly enantioenriched amines, including α-branched and α,α-dibranched amines, α- and β-amino acids, 1,2 and 1,3-amino alcohols and α-trifluoromethyl amines are efficiently synthesized using this methodology.

Pd-Catalyzed directedCH-(hetero)arylation of cyclic α-amino acids: effects of substituents and the ring size

2019 ◽  
Vol 17 (17) ◽  
pp. 4342-4349 ◽  
Author(s):  
Valeriia Hutskalova ◽  
Pavel K. Mykhailiuk
Keyword(s):  
Amino Acids ◽  
Systematic Study ◽  
Ring Size ◽  
Directing Group ◽  
First Time ◽  
Cyclic Amino Acids

A systematic study on the directed Pd-catalyzed (hetero)arylation of 26 substituted cyclic α-amino acids at the C(3)-atom was performed. For the first time, the 7- and 8-membered cyclic amino acids were introduced to C–H activation. 8–Aminoquinoline was used as a directing group.

scholarly journals Synthesis of amino acids and peptides with bulky side chains via ligand-enabled carboxylate-directed γ-C(sp3)–H arylation

2020 ◽  
Vol 11 (1) ◽  
pp. 290-294 ◽  
Author(s):  
Lei Liu ◽  
Yan-Hua Liu ◽  
Bing-Feng Shi
Keyword(s):  
Amino Acids ◽  
Side Chains ◽  
Directing Group

Pd-catalyzed ligand-enabled γ-C(sp3)–H arylation of tert-leucine and its derived peptides without using an external directing group via a less favored six-membered palladacycle is reported.

Mono-selective β-C–H arylation of N-methylated amino acids and peptides promoted by the 2-(methylthio)aniline directing group

2019 ◽  
Vol 17 (22) ◽  
pp. 5595-5600 ◽  
Author(s):  
Thorsten Kinsinger ◽  
Uli Kazmaier
Keyword(s):  
Amino Acids ◽  
Directing Group

2-(Methylthio)aniline (MTA) directed C(sp3)–H functionalisations are efficient and straightforward protocols for the selective β-modification of N-methylated amino acids.

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

scholarly journals Ni(ii)-catalyzed mono-selective ortho-arylation of unactivated aryl C–H bonds utilizing amino acids as a directing group

RSC Advances ◽  
2019 ◽  
Vol 9 (19) ◽  
pp. 10820-10824 ◽  
Author(s):  
Zhanqing Cong ◽  
Feng Gao ◽  
Hong Liu
Keyword(s):  
Amino Acids ◽  
Aryl Iodides ◽  
Directing Group

The nickel(ii)-catalyzed ortho-arylation of unactivated C–H bonds utilizing amino acids as directing groups with aryl iodides or bromides as coupling electrophiles is described.

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