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1 rgy (1.8 kcal/mol) of a cyclobutane versus a cyclopropane.
2 hich upon reductive elimination releases the cyclopropane.
3 he usually inert sites of the donor-acceptor cyclopropane.
4 approach for the synthesis of functionalized cyclopropanes.
5 alogous to that observed with donor-acceptor cyclopropanes.
6 opening cyclizations of donor-acceptor (D-A) cyclopropanes.
7 nd to be stereospecific as in the case of DA cyclopropanes.
8 and enamides to afford 1,2,3-trisubstituted cyclopropanes.
9 catalyzed enantioselective C-H activation of cyclopropanes.
10 olds affords multifunctional, donor-acceptor cyclopropanes.
11 bromide delivered the corresponding alkenyl cyclopropanes.
12 rofuran derivatives from enantioenriched D-A cyclopropanes.
13 electrophiles to generate highly substituted cyclopropanes.
14 in the same fashion with trans-2-methyl-1-X-cyclopropanes.
15 ng generates a range of substituted bicyclic cyclopropanes.
16 ipolar cycloaddition chemistry of azides and cyclopropanes.
17 ts together three acetophenones to construct cyclopropanes.
18 ither diastereomer of di- and trisubstituted cyclopropanes.
19 a highly regioselective aminofluorination of cyclopropanes.
20 access to synthetically useful hydroxymethyl cyclopropanes.
21 cloisomerization of enynes to trisubstituted cyclopropanes.
22 cycloaddition of nitrones to donor-acceptor cyclopropanes.
23 ross-couplings, affording highly substituted cyclopropanes.
24 ve small-size rings such as cyclobutanes and cyclopropanes.
25 cles, we have also demonstrated that racemic cyclopropane 1,1-diesters can undergo dynamic kinetic as
28 ctron (NIPE) spectra of the radical anion of cyclopropane-1,2,3-trione, (CO)3(*-), have been obtained
32 rboxylate relative to methyl 1-azidocarbonyl cyclopropane-1-carboxylate was attributed to a weaker bo
33 ene-1-carboxylate and methyl 1-azidocarbonyl cyclopropane-1-carboxylate were studied by (1)H NMR spec
35 l)amino)isoxazol-5 -yl)-[1,1'-biphenyl]-4-yl)cyclopropane-1-carboxylic acid) in rhesus monkeys to ima
38 roach for the dimerization of donor-acceptor cyclopropanes (2-arylcyclopropane-1,1-dicarboxylates) un
41 -1 to trans,trans-1,2,3-tri(2-(5-phenylfuryl)cyclopropane (4) occurred as a byproduct of treatment wi
42 lkene moiety, subsequent ring-opening of the cyclopropane affords either cyclopentane or cyclohexane
43 This synthesis features a diastereoselective cyclopropane/aldehyde [3+2] cycloaddition to install the
44 irgatusin have been achieved; both rely upon cyclopropane/aldehyde annulation for construction of the
45 n demonstrated for the synthesis of a chiral cyclopropane aldol and a gamma-lactone in a >95:5 diaste
46 f one tripeptide incorporating a fluorinated cyclopropane amino acid (FCAA) analogue is reported.
48 (1), and a less active but extremely stable cyclopropane analog 2, which is currently undergoing pre
49 und: a straightforward decoordination of the cyclopropane and a cationic rearrangement of the three-m
51 -catalyzed annulation between donor-acceptor cyclopropane and N-tosylaziridinedicarboxylate to access
55 loaddition of activated donor-acceptor (D-A) cyclopropanes and aldehydes catalyzed by ((t)Bu-pybox)Mg
60 d styrenes under Rh2(OAc)4 catalysis to give cyclopropanes and dihydrofurans in a highly regioselecti
61 We describe the synthesis of a variety of cyclopropanes and epoxides by combining a readily access
64 n efficient and general entry to unsaturated cyclopropane- and lactone-containing oxylipins of marine
65 Characterization of immune responses to the cyclopropane- and MAMT-deficient strains indicated that
69 yclization reactions of donor-acceptor (D-A) cyclopropanes are recognized as versatile methods for co
76 ss-coupling to form diverse tetrasubstituted cyclopropanes bearing all-carbon quaternary stereocenter
77 resence of a catalytic amount of Sn(OTf)(2), cyclopropanes bearing an aryl or conjugated donor substi
82 t, which subsequently fragments the strained cyclopropane bond to give a lower energy and unreactive
85 d double bond in 1 interacts with the distal cyclopropane bonds in a manner that eventually leads to
86 an be used to produce a product that lacks a cyclopropane but retains a quaternary stereogenic center
87 > n-BuI > n-BuBr approximately (bromomethyl)cyclopropane (but t-Bu2C horizontal lineO < ClSiMe3 in T
89 ric synthesis of trifluoromethyl-substituted cyclopropanes by means of myoglobin-catalyzed olefin cyc
90 bles highly enantioselective Pd(0)-catalyzed cyclopropane C-H functionalization using trifluoroacetim
92 exciting a single molecular conformation of cyclopropane carboxaldehyde above the barrier to C-C sin
93 nd selectively react with olefins, providing cyclopropane carboxaldehydes and 2,3-dihydropyrroles in
95 act with Michael acceptors to give esters of cyclopropane carboxylic acids substituted with p-nitroar
97 The subsequent beta-hydride elimination and cyclopropane cleavage are competitive, determining the e
99 acyclopentene intermediate, in contrast to a cyclopropane cleavage pathway in the reaction with Rh(I)
101 acid induced isomerization of donor-acceptor cyclopropanes, containing an alkenyl moiety and diverse
103 designed and synthesized a series of chiral cyclopropane-containing alpha4beta2-specific ligands tha
105 from Capitella teleta (Ct) in complex with a cyclopropane-containing selective alpha4beta2-nicotinic
107 nabled the multigram synthesis of the chiral cyclopropane core of four drugs (Tranylcypromine, Tasime
108 ppears that commonly cited bond energies for cyclopropane, cyclobutane, and cyclohexane are 3 to 4 kc
109 queous or organic solvent, where ring-opened cyclopropanes, cyclobutanes, and homoallyl products are
110 in a variety of carbocyclic rings, including cyclopropanes, cyclobutanes, cyclopentanes, cyclohexanes
111 ess for (4 + 2)-annulation of donor-acceptor cyclopropanes (DACs) with unsaturated compounds in the p
115 ize the peculiar (1)H NMR chemical shifts of cyclopropane (delta 0.22) and cyclobutane (delta 1.98) w
116 In this work, ring-opening reactions of cyclopropane derivatives under hydrogen catalyzed by met
117 to a number of densely functionalized chiral cyclopropane derivatives, including alpha-cyclopropyl-be
118 n the cyclohexyl system, a small amount of a cyclopropane derived from 1,3-hydrogen migration occurs,
120 he substituents on both the carbinol and the cyclopropane determine both chemo- and stereoselective o
122 tic asymmetric transformation of racemic 1,1-cyclopropane diesters to prepare enantioenriched tetrahy
124 e styrene, we synthesized non-natural phenyl cyclopropanes directly from D-glucose in single-vessel f
125 The reaction proceeds with inversion at the cyclopropane donor site and allows absolute stereochemic
129 transport calculations, which show that the cyclopropane dumbbell gives a higher calculated single-m
130 of spectroscopic techniques reveals that the cyclopropane dumbbell possesses better electronic commun
132 expected to find utility in the synthesis of cyclopropanes, epoxides and their derivatives, as well a
133 The in vivo studies presented here show that cyclopropane fatty acid synthase transcription induced b
134 er sigmaS control encoding, for example, the cyclopropane fatty acid synthase, Cfa, the glycogen synt
136 limidazolium chloride include an increase in cyclopropane fatty acids in the cell membrane, scavengin
138 of unsaturated fatty acids and low levels of cyclopropane fatty acids, (iii) increased membrane fluid
140 synthesis of cis-configured trifluoromethyl cyclopropanes for a broad range of substrates with excel
141 amolecular transformations of donor-acceptor cyclopropanes for cycloisomerizations, formal cycloaddit
142 ough the catalytic oxidative ring-opening of cyclopropanes for the synthesis of 1,3-fluoroacetoxylate
145 t is proposed that the complexes result from cyclopropane fragmentation subsequent to alkene insertio
146 ctive synthesis of novel multifunctionalized cyclopropanes from gamma,delta-epoxy malonates and amine
148 bonyl compounds furnishes the donor-acceptor cyclopropane-fused benzoxa[3.2.1]octane scaffold with ex
149 fforded medicinally relevant benzoindolines, cyclopropane-fused indenopyridines, pyrroloquinolines, o
152 containing Tet-v2.0 reacts selectively with cyclopropane-fused trans-cyclooctene (sTCO) with a bimol
153 ated cyclocarbonylation of a derived alkenyl cyclopropane gave a bicyclic enone that then was hydroge
154 he interactions of the Walsh orbitals of the cyclopropane group with the breaking C-N bonds in N2 los
155 t a dimethyl group at C4 as well as a C9,C19 cyclopropane group, as found in oryzanol, negatively aff
159 ituted C-C bond of the cis-1,2-disubstituted cyclopropane has steric repulsions from the substituent,
161 led acid-catalyzed cleavage of the resulting cyclopropane (HCl), further improvements in a unique int
163 ClbS or an active site residue mutant reveal cyclopropane hydrolase activity that converts the electr
164 a molecular-level view of the first reported cyclopropane hydrolase and support for a specific mechan
165 from Lyngbya majuscula form a beta-branched cyclopropane in the curacin A pathway (Cur), and a vinyl
166 a variety of alkenes, providing cis-dominant cyclopropanes in excellent yields and moderate enantiose
168 of synthetically and biologically important cyclopropanes in high levels of enantio- and diastereose
169 ange of alkenes, affording the corresponding cyclopropanes in high yields with effective control of b
171 straightforward access to highly substituted cyclopropanes in two steps from commercially available a
172 wn that the reactivity of the donor-acceptor cyclopropane increases with the increase of the electron
173 a design in which a reactive donor-acceptor cyclopropane intermediate is generated by in situ conden
175 ific conversion of enantiomerically enriched cyclopropanes into nonracemic heterocycles, we have also
176 rising from an aromatic-like ring current in cyclopropane, involving six electrons in the three C-C b
177 opropane substrate, the substituent from the cyclopropane is away from the reaction center in both pa
179 iles at the donor position of donor-acceptor cyclopropanes is described, representing an inversion of
183 intermolecular reactivity of donor-acceptor cyclopropanes is widely reported, reviews that center on
185 s are reported for methane, ethane, propane, cyclopropane, isobutane, neopentane, tetramethylbutane,
187 ion of a ring-expanded fused cyclobutane (vs cyclopropane), its chemical and structural characterizat
191 al control of host immune activation through cyclopropane modification of TDM as a critical pathogeni
193 ne such alteration in lipid structure is cis-cyclopropane modification of the mycolic acids on trehal
194 ch is governed by rapid isomerization of the cyclopropane moieties at ~1.2 nN, from the force-rate co
196 s a large preference for N2 loss anti to the cyclopropane moiety rather than syn from adducts formed
197 tegic considerations for introduction of the cyclopropane motif in a collection of recent total synth
198 emistry by characterizing an M. tuberculosis cyclopropane-mycolic acid synthase 2 (cmaA2) null mutant
199 ed to enable the synthesis of various unique cyclopropane natural products or use of cyclopropanes as
200 also carried out, and a revised C-H BDE for cyclopropane of 108.9 +/- 1.0 kcal mol(-1) is recommende
201 ase activity that converts the electrophilic cyclopropane of the colibactins into an innocuous hydrol
202 vergent fragment coupling via a nucleophilic cyclopropane opening, a highly diastereoselective formal
203 ules have been synthesized containing either cyclopropane or pyrrolidine rings connecting two fullere
205 , resulting in the formation of a variety of cyclopropanes or C-H insertion products with high stereo
206 esence of MgI2 as Lewis acid, donor-acceptor cyclopropanes or corresponding cyclobutanes were treated
208 Complex molecular architectures containing cyclopropanes present significant challenges for any syn
210 under mild conditions, affording the desired cyclopropane products in high yields with both high dias
211 e same ligand [Fe(1)Cl] afforded the desired cyclopropane products in low yields and poor enantiosele
212 literature, many examples of these polarized cyclopropanes' reactivity with nucleophiles, electrophil
214 Theoretical investigation of cyclopropane-to-cyclopropane rearrangements of sterols indicates a role
216 rrangement, resulting in the cleavage of the cyclopropane ring and the formation of energetically sta
220 ne scaffold (I), the relocation of the fused cyclopropane ring bond and the shifting of the oxygen at
222 catalyzes a cryptic chlorination leading to cyclopropane ring formation in the synthesis of the natu
224 oxin coronatine involves construction of the cyclopropane ring from a gamma-chloro-L-allo-Ile interme
226 pendent enzyme catalyzing the opening of the cyclopropane ring of ACC to give alpha-ketobutyric acid
230 electively at the methylene C-H bonds of the cyclopropane ring over methine or methyl C-H bonds.
232 philic and electrophilic attack on the fused cyclopropane ring results in pyrido[1,2-a]indole and aze
234 20% bicyclogermacrene, a hydrocarbon with a cyclopropane ring that underlines the dual 1,10-/1,11-cy
236 dition of the distal carbon-carbon bond of a cyclopropane ring to the palladium(0) catalyst and the r
237 ctionalized bicyclic sugar unit to which the cyclopropane ring was introduced via carbene addition.
240 addition of Ade to AF followed by hydrolytic cyclopropane ring-opening, indicating the potential for
243 insight into the importance of mycolic acid cyclopropane rings in the PMB and provide the first evid
247 rium tuberculosis cell wall, are modified by cyclopropane rings, methyl branches, and oxygenation thr
250 catalyst, the organocatalytically activated cyclopropanes show an unexpected and highly stereoselect
251 X-ray structure analysis of the resultant cyclopropanes showed that formal migration to the distal
253 nd immunomodulatory function of mycolic acid cyclopropane stereochemistry by characterizing an M. tub
254 e high affinity for hSERT, and the preferred cyclopropane stereochemistry was determined to be (1S,2S
258 In this reaction, cyclobutanones serve as cyclopropane surrogates, reacting in a formal (4+2-1) tr
259 ulating crop, we expressed nine higher plant cyclopropane synthase (CPS) enzymes in the seeds of fad2
261 f which can function as both a cis and trans cyclopropane synthase for the oxygenated mycolates.
262 halose dimycolate (TDM) mediated by proximal cyclopropane synthase of alpha mycolates (pcaA), a proin
264 Here, we demonstrated that mycolic acid cyclopropane synthase PcaA, but not MmaA2, was phosphory
266 at pH 1) relative to N-Boc-CBI containing a cyclopropane (t(1/2) = 133 h at pH 3) may be attributed
267 (4.0 equiv), the spontaneous ring-opening of cyclopropanes takes place to lead to stereoselective (E)
268 ing the synthesis, we isolated an unexpected cyclopropane that presumably stems from a carbonium ion
269 o- and diastereoselectivity to afford unique cyclopropanes that can be further functionalized to prov
271 least substituted carbon-carbon bond of the cyclopropane to form a platinacyclobutane intermediate.
272 vided by their dimerization/combination with cyclopropane to form a six-membered ring reference compo
273 at the CBS-Q level by their combination with cyclopropane to produce a six-member ring reference comp
275 pecifically, upon exposure of donor-acceptor cyclopropanes to alcohols in the presence of a cyclometa
276 c C-C-bond activation of electron-poor vinyl cyclopropanes to generate synthetically useful a1,a3,d5-
279 ic Rh(I)-catalyst systems, amino-substituted cyclopropanes undergo carbonylative cycloaddition with t
281 ene (1) by the single bond in the endo-fused cyclopropane unit of carbene 3 led to similar outcomes.
282 a general strategy for the 1,3-oxidation of cyclopropanes using aryl iodine(I-III) catalysis, with e
284 ocol toward amino-substituted donor-acceptor cyclopropanes via the formal nucleophilic displacement i
285 organocatalyst-promoted ring opening of the cyclopropanes, whereas such reactions have been intensiv
286 y selective construction of poly-substituted cyclopropanes which can be transformed into acyclic deri
287 generation catalyst) gives the corresponding cyclopropane with an enantiomeric ratio of 70/30 and, th
288 exclusively obtained in yield of 51-99% when cyclopropanes with a 2-substituted alkenyl group as a do
289 for the [4 + 2] annulation of donor-acceptor cyclopropanes with acetylenes under the effect of anhydr
290 nulations of malonate-derived donor-acceptor cyclopropanes with aldehydes are unusually broad in scop
292 arbenes, which react with olefins to produce cyclopropanes with excellent diastereo- and enantioselec
293 able of providing access to 1-carboxy-2-aryl-cyclopropanes with high trans-(1R,2R) selectivity and ca
295 opane-1,1-diesters as well as donor-acceptor cyclopropanes with other types of electron-withdrawing a
296 egioselective ring-opening of donor-acceptor cyclopropanes with the Zn-AcOH reductive system was deve
298 drocarbons (including methane, isobutene and cyclopropane) with Ph(2)SiH(2) via sigma-bond metathesis
299 ubstrate spiro[bicyclo[2.2.1]hept-2-ene-7,1'-cyclopropane] with Pt(II) catalysts such as (Me2bpy)PtPh
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