A practical enantioselective N-selective nitroso aldol reaction of α-methylmalonamates with a nitrosoarene is reported. The reaction employs the Takemoto thiourea catalyst for the induction of enantioselectivity, and the corresponding optically active oxyaminated malonamates were obtained in reasonably good yields.
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http://dx.doi.org/10.3762/bjoc.18.25 | DOI Listing |
Beilstein J Org Chem
February 2022
Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram extension, Sitapur Road, P.O. Box 173, Lucknow 226031, India.
A practical enantioselective N-selective nitroso aldol reaction of α-methylmalonamates with a nitrosoarene is reported. The reaction employs the Takemoto thiourea catalyst for the induction of enantioselectivity, and the corresponding optically active oxyaminated malonamates were obtained in reasonably good yields.
View Article and Find Full Text PDFOrg Lett
October 2019
Center of Basic Molecular Science (CBMS), Department of Chemistry , Tsinghua University, Beijing 100084 , China.
An enantioselective primary amine-catalyzed total -selective nitroso aldol reaction (-NA) was achieved through the oxidation of primary aromatic amines to the corresponding nitrosoarenes catalyzed by selenium reagents and 30% HO. This protocol provides a facile and highly efficient access to α-hydroxyamino carbonyls bearing chiral quaternary centers under exceedingly mild and green reaction conditions with high chemo- and enantiocontrol.
View Article and Find Full Text PDFOrg Lett
July 2019
Dipartimento di Chimica e Biologia , Università di Salerno, Via Giovanni Paolo II 132 , 84084 Fisciano , Italy.
Unprecedented α-imino N-acyl pyrazoles were efficiently and selectively prepared through the 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD)-catalyzed reaction of nitrosoarenes with N-acyl pyrazoles via an N-nitroso aldol reaction/dehydration sequence.
View Article and Find Full Text PDFMolecules
February 2019
The Hong Kong Polytechnic University Shenzhen Research Institute, Shenzhen 518000, PR China.
The synthesis of a new CF₃-containing stereogenic atropisomeric pair of ortho-disubstituted biphenyl scaffold is presented. The atropisomers are surprisingly conformationally stable for isolation. X-ray structures show that their stability comes from an intramolecular hydrogen bond formation from their two hydroxyl groups and renders the spatial arrangement of their peripheral CF₃ and CH₃ groups very different.
View Article and Find Full Text PDFOrg Lett
August 2018
Department of Chemistry , Indian Institute of Technology Madras, Chennai 600 036 , Tamil Nadu , India.
An amination reaction of in situ generated gem-difluoro-enolates has been explored with electrophilic nitrogen sources. While their exposure to azodicarboxylates smoothly produced fluorinated α-amino ketones, reaction with nitrosoarenes (nitroso aldol reaction) furnished α-ketoamides in very high yields (up to 94%). The reaction is very fast (typically completed within 5 min) and scalable and tolerates various sensitive functional groups.
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