scholarly journals Peptide late-stage C(sp3)–H arylation by native asparagine assistance without exogenous directing groups

2020 ◽  
Vol 11 (34) ◽  
pp. 9290-9295 ◽  
Author(s):  
Yiyi Weng ◽  
Xingxing Ding ◽  
João C. A. Oliveira ◽  
Xiaobin Xu ◽  
Nikolaos Kaplaneris ◽  
...  
Keyword(s):  
Efficient Method ◽  
Late Stage ◽  
Side Chain ◽  
Directing Group

An efficient method for peptide late-stage C(sp3)-H arylations assisted by unmodified side chain of asparagine (Asn) without any exogenous directing group has been reported.

Selective C–H Bond Fluorination of Phenols with a Removable Directing Group: Late-Stage Fluorination of 2-Phenoxyl Nicotinate Derivatives

ACS Catalysis ◽  
2015 ◽  
Vol 5 (5) ◽  
pp. 2846-2849 ◽  
Author(s):  
Shao-Jie Lou ◽  
Qi Chen ◽  
Yi-Feng Wang ◽  
Dan-Qian Xu ◽  
Xiao-Hua Du ◽  
...  
Keyword(s):  
Late Stage ◽  
Directing Group

Directing group assisted ZnI2-catalyzed cyclopropanation of indoles via 2-furylcarbenoids

2018 ◽  
Vol 5 (11) ◽  
pp. 1768-1771 ◽  
Author(s):  
Wei Chen ◽  
Dong-Sheng Ji ◽  
Yong-Chun Luo ◽  
Zhu-Yin Wang ◽  
Peng-Fei Xu
Keyword(s):  
Efficient Method ◽  
Directing Group

An efficient method for the synthesis of cyclopropane-fused indolines via a Zn2I catalyzed cyclopropanation of indoles and enynones was reported.

Synthesis of the 5-Fluoro-4-hydroxypentyl Side Chain Metabolites of Synthetic Cannabinoids 5F-APINACA and CUMYL-5F-PINACA

Synthesis ◽  
2018 ◽  
Vol 50 (23) ◽  
pp. 4683-4689 ◽  
Author(s):  
Mark Trudell ◽  
Ryan McKinnie ◽  
Tasneam Darweesh ◽  
Phoebe Zito ◽  
Terrell Shields
Keyword(s):  
Efficient Method ◽  
Synthetic Cannabinoids ◽  
Synthetic Cannabinoid ◽  
Protecting Groups ◽  
Side Chain ◽  
Hydroxy Metabolites

An efficient method for the construction of the 5-fluoro-4-hydroxypentyl side chain common to a number of synthetic cannabinoid metabolites was developed. A series of hydroxyl protecting groups was examined to assess the viability as orthogonal protecting groups for epoxidation and regioselective hydrofluorination. The 1-[5-fluoro-4-(diphenyl-tert-butylsilyloxy)]pentyl tosylate was prepared in 67% overall yield (six steps) from pent-4-en-1-ol and was employed for the synthesis of the 4-hydroxy metabolites of the synthetic cannabinoid 5F-APINACA and CUMYL-5F-PINACA.

scholarly journals Merging Directed C−H Activations with High-Throughput Experimentation: Development of Predictable Iridium-Catalyzed C−H Aminations Applicable to Late-Stage Functionalization

2021 ◽  
Author(s):  
Erik Weis ◽  
Maria Johansson ◽  
Pernilla Korsgren ◽  
Belén Martín-Matute ◽  
Magnus J Johansson
Keyword(s):  
Drug Discovery ◽  
High Throughput ◽  
Late Stage ◽  
Functional Group ◽  
Chemical Space ◽  
Material Consumption ◽  
Modern Drug ◽  
High Throughput Experimentation ◽  
Directing Group ◽  
Group Chemical

Herein, we report an iridium-catalyzed directed C−H amination methodology developed using a high-throughput experimentation (HTE)-based strategy, applicable for the needs of automated modern drug discovery. The informer library approach for investigating accessible directing group chemical space for the reaction, in combination with functional group tolerance screening and substrate scope investigations, allowed for the generation of an empirical predictive model to guide future users. Applicability to late-stage functionalization of complex drugs and natural products, in combination with multiple deprotection protocols leading to the desirable aniline matched pairs, serve to demonstrate the utility of the method for drug discovery. Finally reaction miniaturization to a nano molar range highlights the opportunities for more sustainable screening with decreased material consumption.

Late-stage diversification of biologically active pyridazinones via a direct C–H functionalization strategy

2015 ◽  
Vol 13 (2) ◽  
pp. 539-548 ◽  
Author(s):  
Wei Li ◽  
Zhoulong Fan ◽  
Kaijun Geng ◽  
Youjun Xu ◽  
Ao Zhang
Keyword(s):  
Late Stage ◽  
Biologically Active ◽  
Directing Group

Divergent ortho-selective C–H functionalization was successfully established using a pyridazinone moiety as an internal directing group.

Asymmetric Synthesis of Enantiomerically Enriched a-Amino Acids Containing 2-Furyl- and 2-Thienyl-1,2,4-triazoles in the Side-Chain

2014 ◽  
Vol 69 (4) ◽  
pp. 451-460 ◽  
Author(s):  
Ashot S. Saghyan ◽  
Hayarpi M. Simonyan ◽  
Satenik G. Petrosyan ◽  
Anna F. Mkrtchyan ◽  
Lilit V. Khachatryan ◽  
...  
Keyword(s):  
Amino Acids ◽  
Schiff Base ◽  
Asymmetric Synthesis ◽  
Efficient Method ◽  
Enantiomeric Excess ◽  
Side Chain ◽  
Chiral Auxiliaries ◽  
Enantiomerically Pure ◽  
Dehydroamino Acids ◽  
Hydrolysis Of

An efficient method for the asymmetric synthesis of a-amino acids, containing furyl- and thiophenyl-substituted triazoles in their side-chain, is reported. The strategy relies on Michael addition of 3,4,5-substituted 1,2,4-triazoles to the C=C bond of chiral NiII complexes containing the Schiff base formed from dehydroamino acids (dehydroalanine and (E + Z)-dehydroaminobutyric acid) and from chiral auxiliaries, i. e. (S)-2-N-(N0-benzylprolyl)aminobenzophenone and (S)-2-N- (N0-2-chlorobenzylprolyl) aminobenzophenone. The reactions proceeded with good to very good diastereoselectivity. Hydrolysis of the diastereomeric mixtures of metal complexes afforded the enantiomerically pure a-amino acids with high enantiomeric excess (ee> 98%).

ChemInform Abstract: An Efficient Method to Chiral β-Hydroxy Acids: Synthesis of Lipid-A Side Chain.

ChemInform ◽  
2010 ◽  
Vol 31 (9) ◽  
pp. no-no
Author(s):  
E. Nandanan ◽  
Prodeep Phukan ◽  
A. Sudalai
Keyword(s):  
Efficient Method ◽  
Lipid A ◽  
Side Chain ◽  
Hydroxy Acids

scholarly journals γ-Selective C(sp3)–H amination via controlled migratory hydroamination

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Changseok Lee ◽  
Huiyeong Seo ◽  
Jinwon Jeon ◽  
Sungwoo Hong
Keyword(s):  
Computational Methods ◽  
Late Stage ◽  
Alkyl Chain ◽  
Value Added ◽  
Amino Groups ◽  
Olefin Isomerization ◽  
Directing Group ◽  
Walking Mechanism ◽  
Chain Lengths ◽  
Chain Walking

AbstractRemote functionalization of alkenes via chain walking has generally been limited to C(sp3)–H bonds α and β to polar-functional units, while γ-C(sp3)–H functionalization through controlled alkene transposition is a longstanding challenge. Herein, we describe NiH-catalyzed migratory formal hydroamination of alkenyl amides achieved via chelation-assisted control, whereby various amino groups are installed at the γ-position of aliphatic chains. By tuning olefin isomerization and migratory hydroamination through ligand and directing group optimization, γ-selective amination can be achieved via stabilization of a 6-membered nickellacycle by an 8-aminoquinoline directing group and subsequent interception by an aminating reagent. A range of amines can be installed at the γ-C(sp3)–H bond of unactivated alkenes with varying alkyl chain lengths, enabling late-stage access to value-added γ-aminated products. Moreover, by employing picolinamide-coupled alkene substrates, this approach is further extended to δ-selective amination. The chain-walking mechanism and pathway selectivity are investigated by experimental and computational methods.

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