Chiral isoxazolidine-mediated stereoselective umpolung α-phenylation of methyl ketones

2018 ◽  
Vol 16 (46) ◽  
pp. 8940-8943 ◽  
Author(s):  
Norihiko Takeda ◽  
Mizuki Furuishi ◽  
Yuri Nishijima ◽  
Erika Futaki ◽  
Masafumi Ueda ◽  
...  
Keyword(s):  
Methyl Ketones ◽  
One Pot ◽  
Phenyl Ketones

Asymmetric nucleophilic phenylation of N-alkoxyenamine with triphenylaluminium is achieved for the formation of enantioenriched α-phenyl ketones through a one-pot process.

Facile Approach to Geminal Heterodihalogenation. One-Pot Synthesis of α-Bromo-α-Chloro Ketones

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1430-1434
Author(s):  
Ming Bian ◽  
Jin-feng Zhou ◽  
Dong-min Tang
Keyword(s):  
Drug Discovery ◽  
Dimethyl Sulfoxide ◽  
Functional Groups ◽  
Methyl Ketones ◽  
One Pot ◽  
One Pot Synthesis ◽  
Operational Simplicity

An efficient and practical protocol for the geminal heterodihalogenation of methyl ketones by using readily available dimethyl sulfoxide and a combination of HCl and HBr is reported. Control experiments suggested that the acidity of the solution, as well as the oxidizing ability and nucleophilicity of the dimethyl sulfoxide might work cooperatively in ensuring the success of the tandem substitution. Its operational simplicity, easy accessibility, and mild oxidative conditions suggest that the present strategy might be useful for the assembly of bromochloromethyl functional groups in drug discovery.

Reactions of Methyl Ketones and (Hetero)arylcarboxamides with N,N-Dimethylacetamide Dimethyl Acetal. A Simple Metal-Free Synthesis of 2,4,6-Trisubstituted Pyridines

2015 ◽  
Vol 68 (2) ◽  
pp. 184 ◽  
Author(s):  
Benjamin Prek ◽  
Uroš Grošelj ◽  
Marta Kasunič ◽  
Silvo Zupančič ◽  
Jurij Svete ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Single Crystal ◽  
Ammonium Acetate ◽  
Dimethyl Acetal ◽  
Methyl Ketones ◽  
Closed Vessel ◽  
Simple Metal ◽  
One Pot ◽  
X Ray ◽  
Metal Free

Two metal-free syntheses of 2,4,6-trisubstituted pyridines 10a–m and 16a–j are described. N,N,6-Trimethyl-4-(substituted)pyridin-2-amines 10 were prepared from aryl or heteroaryl methyl ketones which were transformed with N,N-dimethylacetamide dimethyl acetal (DMADMA) into enaminones 4a–m, followed by treatment with ammonium acetate to give (Z)-3-amino-1-(substituted)but-2-en-1-ones 5a–m. These were treated with DMADMA under microwave irradiation in a closed vessel at 130°C, to give via intermediates 7–9 the final products 10a–m. N2,N2,N4,N4-Tetramethyl-6-(substituted) pyridine-2,4-diamines 16a–j were prepared in a one-pot synthesis from the corresponding carboxamides 11a–j by treatment with an excess of DMADMA in a closed vessel under microwave irradiation to give via intermediates 12a–j to 15a–j the final products 16a–j. X-Ray single crystal diffractometry studies of the enaminones 5c, 5g, 5i, 5j, and 5m and 2,4,6-trisubstituted pyridines 16a, 16b, 16g, 16i, and 16j were consistent with the expected structures.

scholarly journals One-Pot Conversion of Allylic Alcohols to α-Methyl Ketones via Iron-Catalyzed Isomerization–Methylation

2019 ◽  
Vol 21 (19) ◽  
pp. 7914-7918 ◽  
Author(s):  
Daniel E. Latham ◽  
Kurt Polidano ◽  
Jonathan M. J. Williams ◽  
Louis C. Morrill
Keyword(s):  
Allylic Alcohols ◽  
Methyl Ketones ◽  
One Pot

Difluorohomologization-Halogenation of Methyl Ketones: One-Pot Synthesis of β-Halo-α,α-Difluoroketones

2018 ◽  
Vol 76 (12) ◽  
pp. 983 ◽  
Author(s):  
Xiaoning Song ◽  
Shan Yang ◽  
Xin Wang ◽  
Mang Wang
Keyword(s):  
Methyl Ketones ◽  
One Pot ◽  
One Pot Synthesis

I2–DMSO–PTSA: a simple and metal free oxidative cross coupling of imidazo[1,2-a]pyridines and methylketones

RSC Advances ◽  
2015 ◽  
Vol 5 (25) ◽  
pp. 19418-19425 ◽  
Author(s):  
Madhu Chennapuram ◽  
Narender Reddy Emmadi ◽  
Chiranjeevi Bingi ◽  
Krishnaiah Atmakur
Keyword(s):  
Cross Coupling ◽  
Methyl Ketones ◽  
Simple Metal ◽  
One Pot ◽  
Metal Free

A simple, metal free and selective oxidative cross-coupling promoted by I2–DMSO in presence of PTSA has been developed with the use of imidazo[1,2-a]pyridines (1) and methyl ketones (2) to access 3 in a one pot reaction.

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