[Structure: see text] A catalytic NaI-mediated novel synthesis of 1-bromo-1-nitroalkan-2-ols was carried out by reaction of bromonitromethane with a variety of aldehydes, under very mild conditions. When the reaction was performed with chiral N,N-dibenzyl alaninal, the corresponding enantiopure (1S,2S,3S)-3-dibenzylamino-1-bromo-1-nitrobutan-2-ol was obtained with good stereoselectivity. The structure of this enantiopure bromohydrin was established by X-ray analysis.
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http://dx.doi.org/10.1021/ol062451f | DOI Listing |
Org Biomol Chem
November 2024
Department of Chemistry, Savitribai Phule Pune University (Formerly University of Pune), Ganeshkhind, Pune-411007, India.
Under mild and metal-free reaction conditions, a facile one-pot synthesis of oxygen- and nitrogen-containing benzoheterocycles has been achieved through [4 + 1] annulation of -quinone methides, followed by an oxidation/elimination sequence, efficiently synthesizing functionalized 2,3-dihydrobenzofuran, benzofuran-2(3)-one, and indole derivatives in moderate to good yields (up to 72%). A novel functional group tolerant oxidative Nef reaction utilizes DDQ without a base.
View Article and Find Full Text PDFRSC Adv
January 2024
New Drug Development Center (NDDC), Daegu-Gyeongbuk Medical Innovation Foundation (DGMIF) 80 Cheombok-ro, Dong-gu Daegu 41061 Republic of Korea
A mild and efficient method for photoredox-catalyzed bromonitroalkylation of alkenes is described herein. In this reaction, bromonitromethane serves as a source of both nitroalkyl and bromine for direct and regioselective formation of C-Br and C-C bonds from alkenes, and additional cyclization provides C-C bonds to the cyclopropylamine core as an LSD1 inhibitor.
View Article and Find Full Text PDFEnviron Sci Technol
July 2016
Laboratori d'Electroquímica dels Materials i del Medi Ambient, Departament de Química Física, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain.
Electrocoagulation (EC) has long been considered a phase separation process, well suited for industrial wastewater treatment since it causes a quick, drastic decay of organic matter content. This research demonstrates that EC also behaves, at least for some molecules like the industrial preservative bronopol, as an effective transformation technology able to yield several breakdown products. This finding has relevant environmental implications, pointing to EC as a greener process than described in literature.
View Article and Find Full Text PDFJ Org Chem
September 2015
Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Ferrara, Via Fossato di Mortara 17, 44121 Ferrara, Italy.
The asymmetric synthesis of functionalized nitrocyclopropanes has been achieved by a one-pot, four-step method catalyzed by (S)-diphenylprolinol TMS ether, which joins two sequential domino reactions, namely a domino sulfa-Michael/aldol condensation of α,β-unsaturated aldehydes with 1,4-dithiane-2,5-diol, and a domino Michael/α-alkylation reaction of the derived chiral dihydrothiophenes with bromonitromethane. The title compounds were obtained in 27-45% yields, with high levels of diastereoselectivity (93:7 to 100:0 dr) and generally good enantioselectivities (up to 95:5 er).
View Article and Find Full Text PDFChem Sci
January 2015
Department of Chemistry and Vanderbilt Institute of Chemical Biology Vanderbilt University, Nashville, Tennessee 37235.
Peptides consisting of D-amino amides are highly represented among both biologically active natural products and non-natural small molecules used in therapeutic development. Chemical synthesis of D-amino amides most often involves approaches based on enzymatic resolution or fractional recrystallization of their diastereomeric amine salts, techniques that produce an equal amount of the L-amino acid. Enantioselective synthesis, however, promises selective and general access to a specific α-amino amide, and may enable efficient peptide synthesis regardless of the availability of the corresponding α-amino acid.
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