The Bent Bonds of Cubane
Sign Up to like & getrecommendations! Published in 2017 at "European Journal of Organic Chemistry"
DOI: 10.1002/ejoc.201700427
Abstract: The carbon–carbon bonding in cubane is shown not to be along the C–C vectors between carbon atoms at the corners of a cube. Instead, the bonding is “bent” as seen in a new single-crystal X-ray… read more here.
Keywords: bonds cubane; cyclopropane; chemistry; bent bonds ... See more keywords
Synthesis and rearrangement reactions of 1,4-dihydrospiro[1,4-methanonaphthalene-9,1′-cyclopropane] derivatives
Sign Up to like & getrecommendations! Published in 2018 at "Tetrahedron"
DOI: 10.1016/j.tet.2018.07.060
Abstract: Abstract Reactions of benzyne with ester derivatives of spiro[2.4]hepta-4,6-dien-1-ylmethanol were performed. By rearrangement reaction of cyclopropyl methanol units of ((1s*,1′R*,2R*,4′S*)-1′,4′-dihydrospiro[cyclopropane-1,9'-[1,4]methanonaphthalen]-2-yl) methyl 3,5-dinitrobenzoate (13) and its isomer (14), corresponding allyl chlorides were obtained. Two rearrangement products… read more here.
Keywords: synthesis rearrangement; rearrangement reactions; cyclopropane; reactions dihydrospiro ... See more keywords
Localization of Cyclopropane Modifications in Bacterial Lipids via 213 nm Ultraviolet Photodissociation Mass Spectrometry.
Sign Up to like & getrecommendations! Published in 2019 at "Analytical chemistry"
DOI: 10.1021/acs.analchem.9b01038
Abstract: Subtle structural features in bacterial lipids such as unsaturation elements can have vast biological implications. Cyclopropane rings have been correlated with tolerance to a number of adverse conditions in bacterial phospholipids. They have also been… read more here.
Keywords: cyclopropane; ultraviolet photodissociation; 213 ultraviolet; bacterial lipids ... See more keywords
Cyclopropane Hydrogenation vs Isomerization over Pt and Pt–Sn Intermetallic Nanoparticle Catalysts: A Parahydrogen Spin-Labeling Study
Sign Up to like & getrecommendations! Published in 2020 at "Journal of Physical Chemistry C"
DOI: 10.1021/acs.jpcc.0c02493
Abstract: Hyperpolarized propane produced by heterogeneous hydrogenation of cyclopropane with parahydrogen has been proposed as a safe inhalant for sensitivity-enhanced in vivo magnetic resonance imaging. Th... read more here.
Keywords: intermetallic nanoparticle; cyclopropane; hydrogenation; cyclopropane hydrogenation ... See more keywords
3,4-Annulated Indoles via Tandem Cyclopropane Ring-Opening/Conia-ene and Michael Addition/Conia-ene Reactions.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01810
Abstract: 4-Alkynyl indoles, when treated with a benzylidene malonate or a donor-acceptor cyclopropane in the presence of a zinc halide, furnished 3,4-hexannylated or 3,4-heptannulated products, respectively, in fair to excellent yields. The reaction proceeds via a… read more here.
Keywords: ene; via tandem; conia ene; cyclopropane ... See more keywords
Sulfoxonium Ylides in Aminocatalysis: An Enantioselective Entry to Cyclopropane-Fused Chromanol Structures
Sign Up to like & getrecommendations! Published in 2022 at "Organic Letters"
DOI: 10.1021/acs.orglett.2c02204
Abstract: The 1,1a,2,7b-tetrahydrocyclopropa[c]chromene, arising from fusion of chromane and cyclopropane rings is the core of medicinally relevant compounds. Engaging sulfoxonium ylides in enantioselective aminocatalytic reactions for the first time, a convenient entry to this scaffold is… read more here.
Keywords: enantioselective entry; cyclopropane; ylides aminocatalysis; aminocatalysis enantioselective ... See more keywords
Ir-Catalyzed Biomimetic Photoisomerization of Cyclopropane in Lathyrane-Type Euphorbia Diterpenes.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c03172
Abstract: An efficient Ir-catalyzed biomimetic method for photoisomerization of cyclopropane in lathyrane-type Euphorbia diterpenes is reported. Lathyrane diterpenes featuring the trans-fused cyclopropane (1a-5a) were successfully prepared from cis-cyclopropane lathyranes (1-5) in excellent yields by this stereochemical… read more here.
Keywords: cyclopropane; lathyrane type; lathyrane; photoisomerization cyclopropane ... See more keywords
A Donor-Acceptor Cyclopropane by Intramolecular C(sp3)-H Activation at a Cyclic(alkyl)(amino)carbene Center and Its Fascinating Ring-Opening Chemistry.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c01072
Abstract: Virtually irreversible intramolecular C-H activations are deleterious for aza-carbenes. A picolyl-tethered cyclic(alkyl)(amino)carbene (CAAC) isomerizes into a donor-acceptor cyclopropane in this manner but restores the CAAC status by retro-C-H activation in the presence of trapping agents… read more here.
Keywords: alkyl amino; amino carbene; chemistry; cyclic alkyl ... See more keywords
Amino Acid-Based Synthesis and Glycosidase Inhibition of Cyclopropane-Containing Iminosugars
Sign Up to like & getrecommendations! Published in 2020 at "ACS Omega"
DOI: 10.1021/acsomega.0c04589
Abstract: Synthesis of four iminosugars fused to a cyclopropane ring is described using l-serine as the chiral pool. The key steps are large-scale preparation of an α,β-unsaturated piperidinone followed by completely stereoselective sulfur ylide cyclopropanation. Stereochemistry… read more here.
Keywords: based synthesis; acid based; amino acid; cyclopropane ... See more keywords
A radical S-adenosyl-L-methionine enzyme and a methyltransferase catalyze cyclopropane formation in natural product biosynthesis
Sign Up to like & getrecommendations! Published in 2018 at "Nature Communications"
DOI: 10.1038/s41467-018-05217-1
Abstract: Cyclopropanation of unactivated olefinic bonds via addition of a reactive one-carbon species is well developed in synthetic chemistry, whereas natural cyclopropane biosynthesis employing this strategy is very limited. Here, we identify a two-component cyclopropanase system,… read more here.
Keywords: biosynthesis; cyclopropane; methyltransferase; adenosyl methionine ... See more keywords
A novel type of donor–acceptor cyclopropane with fluorine as the donor: (3 + 2)-cycloadditions with carbonyls
Sign Up to like & getrecommendations! Published in 2022 at "Chemical Science"
DOI: 10.1039/d2sc00302c
Abstract: gem-Difluorocyclopropane diester is disclosed as a new type of donor–acceptor cyclopropane, which smoothly participates in (3 + 2)-cycloadditions with various aldehydes and ketones. This work represents the first application of gem-difluorine substituents as an unconventional… read more here.
Keywords: donor; donor acceptor; acceptor cyclopropane; cyclopropane ... See more keywords