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1 y the substitution at the C3 position of the aziridine.
2 the allene to a strained bicyclic methylene aziridine.
3 e >99%) from enantiopure trans-disubstituted aziridine.
4 so enables cross-coupling with Boc-protected aziridines.
5 y was achieved with the activation of cyclic aziridines.
6 2-azido-aminoalcohols, diaminoalcohols, and aziridines.
7 palladium-catalyzed cross-coupling of intact aziridines.
8 fied Stille conditions to afford substituted aziridines.
9 tric inductions and higher overall yields of aziridines.
10 ylmethyl imines with diazoesters to give cis-aziridines.
11 ared by the oxidative addition of Ni(0) with aziridines.
12 y2) generates trans-alpha-lithiated terminal aziridines.
13 tained with both alkyl- and aryl-substituted aziridines.
14 -catalyzed Csp(3)-Csp(3) cross-coupling with aziridines.
15 -98 %) and mostly >90 % optically active cis-aziridines.
16 oenriched 2-arylphenethylamines from racemic aziridines.
17 ctive construction of complex trisubstituted aziridines.
18 means for the synthesis of alkyl-substituted aziridines.
19 been studied using the structurally similar aziridines.
20 nd application in dynamic systems other than aziridines.
21 xchange are described for carbon-substituted aziridines.
22 dine opening of tosyl-activated cyclopentene aziridine 2 and optical resolution of racemic 1 with 10-
24 ate and methanediphosphonate anions afforded aziridine 2-methyl diphosphates and methanediphosphonate
25 nique reactivity of the resulting N-acylated aziridine-2-carbonyl peptides facilitates their subseque
27 a-GalNAc-Ser linkage via the ring opening of aziridine-2-carboxamides with pyranose C1-O-nucleophiles
28 sters, and unexpectedly, the N-Boc-protected aziridine-2-carboxylate 16b with a phenyl substituent in
30 mediated by the imino-BOROX catalyst to give aziridine-2-carboxylic esters with very high diastereo-
32 ion and afforded, upon deprotection, the N-H aziridine 24 in 18-32% overall yield for the three steps
33 y classes of nitrogen heterocycles including aziridines, 2H-azirines, pyrrolidines, and piperidines.
34 under otherwise identical conditions, vinyl aziridine 3a and aldehydes 2a-2l engage in reductive cou
35 Using enantiomeric iridium catalysts, vinyl aziridine 3a reacts with unprotected chiral 1,3-diols 1m
36 of N-(p-nitrophenylsulfonyl) protected vinyl aziridine 3a with primary alcohols 1a-1l to furnish bran
39 indole fragment, (b) formation of hexacyclic aziridine 80 from the reaction of cyanide with intermedi
40 -opening of the aziridinium ion derived from aziridine 80, and (d) base-promoted skeletal rearrangeme
47 l for the three-component reaction driven by aziridine aldehyde dimers has predictive value for diffe
48 syn-stereoselectivity from readily available aziridine aldehyde dimers in the Petasis borono-Mannich
49 he multicomponent conversion of amino acids, aziridine aldehyde dimers, and isocyanides into chiral p
51 a range of functionalized isocyanides in the aziridine aldehyde-driven multicomponent synthesis of pi
52 ibitor calpastatin have motivated the use of aziridine aldehyde-mediated peptide macrocyclization tow
54 The cyclization chemistry centers on using aziridine aldehydes in a multicomponent reaction with pe
56 y, the synthesis and reactivity of methylene aziridines, allene oxides/spirodiepoxides, methylene sil
57 Here we show that the reduced amidicity of aziridine amide bonds provides an entry point for the si
58 the latter obtained by a Lewis acid-promoted aziridine amino acid ring opening with 4-boronated indol
60 rization of five racemic and two enantiopure aziridine analogues of PSPP and the evaluation of their
61 m the palladium(II) species bearing both the aziridine and aryl groups to form the hindered C-C bond.
63 rization of enynes, [3 + 2] cycloaddition of aziridines and alkenes, and [4 + 2] hetero-Diels-Alder c
64 he phosphine-mediated [3 + 3] annulations of aziridines and allenes are experimentally simple reactio
65 ioselective ring-opening of chiral activated aziridines and azetidines with alcohols to nonracemic be
66 ation processes, leading to the synthesis of aziridines and beta-lactams (respectively), and is sugge
67 cross-coupling between tosyl-protected alkyl aziridines and commercially available (hetero)aryl iodid
68 hesized manno-epi-cyclophellitol epoxide and aziridines and demonstrate their covalent modification a
69 ring-opening of the corresponding activated aziridines and epoxides with amines followed by p-toluen
72 The reaction proceeds through a mixture of aziridines and oxazolines, which provides the trans-oxaz
73 vestigated using a variety of functionalized aziridines and phenols to determine the scope of the rea
74 report a [3 + 3] ring expansion of bicyclic aziridines and rhodium-bound vinyl carbenes to form comp
75 of the substituent in the 3-position of the aziridine, and whether the substituent in the 3-position
76 an), which is known to carbonylate epoxides, aziridines, and beta-lactones, was used to catalyze the
77 es, which induce the direct formation of the aziridines, and stereochemistry of the olefin is retaine
78 clopropanols, cyclopropenols and epoxides or aziridines are applied to the synthesis of acyclic versu
79 to add to the Si-face of the imine when cis-aziridines are formed and both to add to the Re-face of
83 nto azetidine derivatives, whereas methylene aziridines are the products resulting from alkylallenes.
85 ormational transitions, which in the case of aziridines arise from inversion at the nitrogen center.
86 e-component coupling involving N-substituted aziridines, arynes, and water promoted by trifluoroaceti
87 reactions are the first reported examples of aziridines as reaction partners in nucleophilic phosphin
89 er formation was explored with small N-alkyl aziridines, azetidines, pyrrolidines, and piperidines.
90 rently exist: doubly-activated molecules and aziridine based molecules, each of which employs a diffe
96 n rates of cyclophellitol and cyclophellitol aziridine-both covalent retaining beta-glucosidase inhib
97 of heretofore-unknown (o-fluoroaryl)sulfonyl aziridine building blocks with an array of amino alcohol
98 CH(2)OH/CH(3)CN desilylated a simple N-TBDPS aziridine but caused nucleophilic cleavage at C(1) as we
99 Selective labeling with fluorescent beta-aziridine but not beta-epoxide ABPs identifies the acid/
100 onfiguration at the terminal position of the aziridine by way of aziridine ring opening by Ni (invers
101 The S(N)2-type ring-opening of N-activated aziridines by anilines followed by Pd-catalyzed annulati
103 st accelerates the ring opening of aliphatic aziridines by trimethylsilylazide, inducing nucleophilic
104 that heterolysis at C(10) is faster than at aziridine C(1), in contrast to the behavior of typical a
107 If necessary, the N-4-nosyl Hough-Richardson aziridine can be isolated by filtration in a very good y
110 nation reaction of nonactivated alkynes with aziridines, catalyzed by Lewis or Bronsted acids, to for
117 describe a detailed mechanistic study of the aziridine cross-coupling reaction and the role of EDO li
119 ctive strategies for ring-opening of the new aziridines, deprotection of the Ts group, and subsequent
120 re alpha-acyl-beta-amino acid and 2,2-diacyl aziridine derivatives efficiently from Cu(OTf)(2) + 1,10
121 tion of fluorescent manno-epi-cyclophellitol aziridine derivatives enabled activity-based protein pro
122 philic ring-opening reactions of N-activated aziridine derivatives with thiols, beta-thioglycosyl thi
123 expansion of vinyloxiranes, -thiiranes, and -aziridines described in the literature from 1964 to 2013
124 ridine substitution patterns show that alkyl aziridines display similar reactivity to alkynyl aziridi
125 ubstituent groups on the biologically active aziridine do not function as TbNTR or TbCPR-activated pr
128 high asymmetric inductions as seen with cis-aziridines, enabling the development of an unprecedented
130 nd to react at accelerated rates relative to aziridine exclusively by means of the a Menshutkin-type
133 lyzed SN2-type ring-opening of the activated aziridine followed by a concomitant 5-exo-dig cyclizatio
134 alkylation of 2-vinylindoles with activated aziridines followed by an intramolecular aza-Michael rea
135 rmation of gram quantities of a key tricylic aziridine from a challenging photochemical cascade react
137 direct synthesis of N-phosphorus-substituted aziridines from alkenes with dinitrogen as the byproduct
139 ubstituted imines, the optical purity of the aziridines from all of the imine substrates could be enh
141 oselective synthesis of trisubstituted vinyl aziridines from these chiral sulfinamides, simply by cha
143 been elaborated, affording an unprecedented aziridine-fused spiro[imidazolidine-4,3'-oxindole] frame
144 ed aryl bromides and tertiary organometallic aziridines, generated from sulfinylaziridines by sulfiny
145 idines display similar reactivity to alkynyl aziridines, giving insight into mechanistic possibilitie
146 or the modified Wenker cyclization to afford aziridines has been achieved using biphasic conditions f
147 p-assisted C7 C-C coupling of indolines with aziridines has been developed by merging C-H activation
149 A series of novel, highly substituted N-PMP aziridines have been accessed in high yields by palladiu
151 nd nitrogen in the formation of oxiranes and aziridines; however, such reactivity is not known betwee
153 ehydes were examined and found to give trans-aziridines in 60-88% yield with 60-98% ee and trans/cis
154 h aryl aldehydes were screened to give trans-aziridines in 73-90% yield with 82-99% ee and trans/cis
156 MEDAM imines can be deprotected to give N-H aziridines in all cases except for some electron-rich ar
157 uents leads to the quantitative formation of aziridines in clean solid-to-solid reactions despite ver
158 selective formation of either functionalized aziridines in dimethylformamide (through direct bromide
160 c carbamates into [4.1.0]-carbamate-tethered aziridines in good yields and with ee values of up to 92
163 forming the desired N-phosphorus-substituted aziridines in moderate to high yields and good enantiose
166 [1,2-a]pyridine ring via the formation of an aziridine intermediate in Mannich bases derived from imi
168 yridinium perchlorate to generate a bicyclic-aziridine intermediate, which is transformed under aziri
169 nolithium-mediated conversion of beta-alkoxy aziridines into substituted allylic sulfonamides, use of
170 N-bound phenyl rings of amines, imines, and aziridine is achieved in the presence of H(2) and B(C(6)
172 r the oxidative annulation of indolines with aziridines is accomplished employing the combination of
177 ] with Me3SiCl releases the N-functionalized aziridine Me3SiN(CH2CHPh) while simultaneously generatin
179 g HSQC NMR peaks were identified in the (13C)aziridine-modified enzyme, corresponding to detection of
180 were replaced, the former with a substituted aziridine moiety and the latter with an NCO-alkyl residu
184 h a N-tosyl group, rendering these alpha-CF3-aziridines much more susceptible to nucleophilic ring op
186 re the development of a new synthesis of the aziridine necessary for the aziridine--pi-nucleophile cy
188 to serve as protecting groups for the labile aziridine nitrogen found within the highly sensitive azi
191 bstrate established that ring opening of the aziridine occurs with inversion of stereochemistry.
192 ped a short and practical synthesis of 1 via aziridine opening of tosyl-activated cyclopentene azirid
193 rough electrochemical amination, Cu-mediated aziridine opening, and a remarkable base-induced macrola
194 trideoxy-L-hex-2-enopyranosides, followed by aziridine opening, leads to 3-amino-3-N-,4-O-carbonyl-2,
199 tion, the effect of fluorine substitution at aziridine positions other than nitrogen was studied.
200 Compound A (CpdA) is a stable analogue of an aziridine precursor from the African shrub Salsola tuber
205 s were utilized to afford the functionalized aziridine products as single diastereoisomers with reten
206 e of regio- and enantiocontrol to afford the aziridine products in good to excellent yields in highly
207 strated through derivatization of the chiral aziridine products to obtain a diverse array of function
211 unique strain and structure of the methylene aziridine promotes a ring-opening/ring-closing cascade t
215 rine substitution at the carbon positions of aziridine results in profound enhancements of the rate o
216 nd carbenes with strained bicyclic methylene aziridines results in a formal [3+1] ring expansion to y
217 ladium(0) on the less-hindered carbon of the aziridine ring and that alkene insertion occurs in a syn
218 in DMA led to regioselective opening of the aziridine ring at C2 to give the corresponding bicyclic
220 rans-oxazolines following in situ Heine-type aziridine ring expansion upon treatment with BF(3).OEt(2
221 tions of these genes, a possible pathway for aziridine ring formation in the azecimicins can now be p
222 odular one-pot, sequential protocol using an aziridine ring opening and intramolecular nucleophilic a
223 terminal position of the aziridine by way of aziridine ring opening by Ni (inversion), transmetalatio
224 kylation to effect regio- and stereospecific aziridine ring opening by oxygen, halogen, sulfur, and n
225 ine intermediate, which is transformed under aziridine ring opening conditions to the key intermediat
227 investigation of a regio- and stereospecific aziridine ring opening reaction presents new synthetic t
229 ereoselective epoxidation and opening of the aziridine ring with hydrazoic acid afforded the 2-azidoc
230 or nucleophile-dependent ring-opening of the aziridine ring yields functionalized 1,2- and 1,3-diamin
231 oped by utilizing a newly discovered ethynyl aziridine ring-opening reaction in a longest linear sequ
233 new flow reaction could be combined with an aziridine-ring-opening reaction to give highly functiona
234 ks for tripeptide controls, a small molecule aziridine self-polymer mimetic, and a cysteine-minus con
235 s removal of the noncovalently protein-bound aziridine self-polymer using a novel chelating dialysis
238 ctural features such as the nature of the C2 aziridine substituent and the nature of the electrophile
241 l aldehyde gave a 71% yield and 95% ee of an aziridine that was found to be the cis- and not the tran
243 thetically exploited oxiranes and thiiranes, aziridines that lack electron-withdrawing substituents,
244 ds contain two electronically differentiated aziridines that undergo highly regioselective ring openi
245 of (R)-beta(3)-DOPA and L-DOPA from the same aziridine, the former by SmI2-mediated reductive opening
246 on of the nature of the N-substituent of the aziridine, the nature of the substituent in the 3-positi
248 triplet sensitizers that selectively produce aziridines through the spin-selective photogeneration of
249 t of nucleophilic iodide ring opening of the aziridine to generate an iodoamine as the active electro
250 gle catalyst transforms a racemic mixture of aziridines to a pair of regioisomeric products, each in
252 e we describe a new tool, methylthiocarbonyl-aziridine, to install acetyl-Lys mimics site-specificall
253 were developed for deprotection of the N-DAM-aziridines under acidic conditions without causing an ac
255 -, tri-, and tetrasubstituted olefins to N-H aziridines using O-(2,4-dinitrophenyl)hydroxylamine (DPH
256 ring opening of non-activated 2-substituted aziridines via intermediate aziridinium salts will be de
257 probes elaborated from an inhibitor with an aziridine warhead were applied to the identification and
259 tions, N-o-(trifluoromethane)benzenesulfonyl aziridine was efficiently ring-opened to afford the amin
260 us reactions between the five components, an aziridine was formed in 85% yield and 98% ee and only tw
262 1-alkyl-2-(methyl/phenyl)-3-(trifluoromethyl)aziridines was developed starting from the corresponding
263 ese newly synthesized nonactivated alpha-CF3-aziridines was evaluated by applying N-protonation or N-
266 catalyst; however, in those cases where cis-aziridines were formed, the configuration was opposite f
269 this can be particularly pronounced with cis-aziridines where a nearly equal mixture of the two is ob
270 generate separable, diastereomeric bicyclic-aziridines, which are then independently transformed to
271 the observed absolute stereochemistry of the aziridines, which undergo nucleophilic ring opening to y
272 have found that N-diphenylphospinyl and N-H aziridines, while participating in the initial ring-open
273 col is also equally effective for the phenyl aziridine with excellent regio- and stereoselectivity.
274 ia in situ formed N-4-nosyl Hough-Richardson aziridine with nitrogen nucleophiles under mild conditio
275 lso been synthesized via the ring-opening of aziridines with 2-bromobenzyl alcohols and -mercaptan, r
276 gh an S(N)2-type ring-opening of N-activated aziridines with 2-bromobenzylamine followed by a hithert
277 type ring opening of enantiopure N-activated aziridines with 2-bromoindoles followed by copper-cataly
278 been developed by ring-opening of activated aziridines with 2-hydroxyphenyl acrylates and 2-aminophe
281 domino ring-opening cyclization of activated aziridines with aryl and alkyl isothiocyanates has been
283 ing of unsubstituted and 2-alkyl-substituted aziridines with arylboronic acid nucleophiles is present
284 ions involve a regiospecific ring opening of aziridines with benzimidazoles to give benzoimidazolylet
285 the thermal C-C bond cleavage of unactivated aziridines with beta-bromo-beta-nitrostyrene, followed b
286 re applied in the cycloaddition reactions of aziridines with carbon dioxide (CO(2)) or carbon disulfi
287 lyzed S(N)2-type ring opening of substituted aziridines with electron-rich arenes/heteroarenes to pro
289 -N-acyloxazolidinones to give trisubstituted aziridines with excellent diastereo- and enantioselectiv
290 synthetically useful chiral [3.1.0]-bicyclic aziridines with high diastereo- and enantioselectivity.
291 catalyzed SN2-type ring opening of activated aziridines with indoles having substitutions at 3- and o
292 eoselective deprotonation of simple terminal aziridines with lithium 2,2,6,6-tetramethylpiperidide (L
293 ring-opening cyclization (DROC) of activated aziridines with malononitrile in excellent yield and ste
294 The intramolecular cyclization reactions of aziridines with pi-nucleophiles can be a useful route to
295 and aliphatic aldehydes both gave the trans-aziridines with the same absolute configuration with the
296 me imines with diazoacetamides to give trans-aziridines with the same high asymmetric inductions as s
297 the C-N cleavage product is observed for all aziridines with the strongly N-activating p-toluene sulf