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4 forward method for generation of versatile 1-alkenyl-1,1-heterobimetallic intermediates and their app
6 duced herein is a practical application of 1-alkenyl-1,1-heterobimetallic intermediates in the synthe
11 the in situ synthesis of (E)-3-substituted 6-alkenyl-1,2,4,5-tetrazine derivatives through an elimina
12 n includes a rhodium-catalyzed reaction of 4-alkenyl-1-sulfonyl-1,2,3-triazoles featuring an unusual
14 rmation to the preparation of a variety of N-alkenyl 2-pyridonyl ether analogues, which have the pote
15 nal studies suggest that the desired 5-exo N-alkenyl 2-pyridonyl ethers are formed reversibly in the
16 tramolecular ring closures by inclusion of 2-alkenyl, 2-aryl, or 2-oximinyl functionality reacted rat
21 tereospecifically the E or Z isomer of the 5-alkenyl-4-iminohydantoin products from the corresponding
22 ne-complexed lithiated carbamates with trans-alkenyl-9-BBN derivatives followed by addition of aldehy
24 Z-disubstituted alkenyl-, 1,1-disubstituted alkenyl-, acyclic, or heterocyclic trisubstituted alkeny
26 he three-component addition cascade, and the alkenyl addition product can readily be converted into d
27 ere a rhodium-catalyzed asymmetric conjugate alkenyl addition with subsequent silyl trapping and a Mu
29 n of highly substituted allylic alcohols and alkenyl alcohols by means of a single catalytic system.
31 as it disengages during the isomerization of alkenyl alcohols when additional substituents are presen
33 (50), 230 microM), by endogenously occurring alkenyl aldehydes (EC(50): 4-hydroxynonenal 19.9 microM,
36 f disulfide bonds whereas the actions of the alkenyl aldehydes and 15d-PGJ(2) were not reversed, sugg
38 sses to provide aryl-aryl, alkenyl-aryl, and alkenyl-alkenyl coupled products by exploiting a common
40 ilylative iodination reaction, as well as an alkenyl-alkenyl silicon-based cross-coupling reaction.
42 n cross-coupling reactions between aromatic, alkenyl, alkynyl, and alkyl substrates in library or ind
47 sigma-bond metathesis between the resultant alkenyl aluminum species and HBpin, which acts to drive
49 ates containing hindered alpha-methyl, alpha-alkenyl amino acids and (ii) the ring-closing olefin met
55 ed-anti-[2.2]metacyclophanedienes (CPD) with alkenyl and alkynyl internal (8,16) groups is described
56 cyclic ketones from the coupling reaction of alkenyl and allenyl cycloalkanols with aryl diazonium sa
59 played a striking longitudinal gradient with alkenyl and hydroxyalkenyl glucosinolates enriched in th
60 fers regiospecific access to acyl/aryl, acyl/alkenyl, and acyl/alkoxy gold carbenes by in situ expuls
61 he hydroacylation of vinylphenols with aryl, alkenyl, and alkyl aldehydes to form branched products w
64 as amenable to a broad range of alkyl, aryl, alkenyl, and alkynyl organomagnesium, -zinc, -aluminum,
65 studies have shown compatibility with alkyl, alkenyl, and alkynyl, aromatic, and several heteroaromat
68 hyde input; electron rich and poor aromatic, alkenyl, and branched and unbranched alkyl aldehydes all
70 methods for C-C bond formation using aryl-, alkenyl- and alkynylboronic acids under transition-metal
71 is illustrated herein for the synthesis of o-alkenyl- and o-arylphenones, which have potential for th
73 rant of a broad range of aryl-, heteroaryl-, alkenyl-, and alkyltrifluoroborates as well as structura
74 Starting from aryl-, heteroaryl-, alkynyl-, alkenyl-, and alkyltrifluoroborates, a library of highly
76 and tandem cyclizations of alpha-halo-ortho-alkenyl anilides bearing an additional substituent on th
77 Et(3)B/air, rt) of racemic alpha-halo-ortho-alkenyl anilides provide 3,4-dihydroquinolin-2-ones in h
79 counterintuitive Lewis base stabilization of alkenyl anions in anionic cyclization) and nanomaterials
81 stituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts combine to form syn-1,3-car
82 al for many terminal epoxides bearing alkyl, alkenyl, aryl, alkoxy, chloromethyl, phthalimido, and ac
84 cessfully applied to the synthesis of alkyl, alkenyl, aryl, heteroaryl, and cyclopropyl ethers, mixed
85 oss-coupling processes to provide aryl-aryl, alkenyl-aryl, and alkenyl-alkenyl coupled products by ex
86 ted alpha-hydroxystannanes cross-couple with alkenyl/aryl/heteroaryl iodides in moderate to good yiel
87 vated carbon-carbon multiple bond to give an alkenyl Au intermediate, notwithstanding the fact that t
89 e performed to afford structurally complex Z-alkenyl-B(pin) as well as Z-alkenyl iodide compounds rel
91 variety of robust alkenyl-(pinacolatoboron) [alkenyl-B(pin)] compounds that can be either purchased o
92 Here, we show that dienes containing an E-alkenyl-B(pinacolato) group, widely used in catalytic cr
93 y ring-closing metathesis of the resultant N-alkenyl beta-amino esters, reduction to the correspondin
94 mediated dihydroxylation of a range of beta-alkenyl-beta-hydroxy-N-acyloxazolidin-2-ones results in
95 tively high barriers to rotation round the N-alkenyl bond (DeltaG() rotation >20 kcal mol(-1)) were s
99 aster or slower than the estimated rate of N-alkenyl bond rotation in the derived radicals, depending
104 se of 15 mol % of (S)-VAPOL as the catalyst, alkenyl boronates as nucleophiles, ethyl glyoxylate as t
105 yze the enantioselective Petasis reaction of alkenyl boronates, secondary amines, and ethyl glyoxylat
106 ynes couple with various substituted alkynyl/alkenyl boronates/boronic acids by this procedure to fur
108 the Csp-Csp2 coupling of alkynyl bromide and alkenyl boronic acid to provide conjugated 1,3-enynes.
109 o-step process involves etherification of an alkenyl boronic acid with N-hydroxyphthalimide followed
111 e with aryl, pi-electron-rich heteroaryl, or alkenyl boronic acids in the presence of stoichiometric
112 atalyzed conversion of aryl, heteroaryl, and alkenyl boronic acids into sulfinate intermediates, and
114 the conversion of terminal alkenes to trans-alkenyl boronic esters using commercially available cate
116 s-coupling of the vinylic stannane 4 and the alkenyl bromide 5 to produce a highly functionalized die
118 3-enyl)hydroxylamine derivatives and aryl or alkenyl bromides afford cis-3,5- and trans-4,5-disubstit
120 e involves treating a NH-indole with various alkenyl bromides using a combination of 10 mol % of copp
129 at sn-1 of an ether bond to an alkyl or a 1Z alkenyl chain and that of a sn-2-esterified n-3 fatty ac
130 in which a borane prepared from the pendent alkenyl chain of the cyclohexene domain was reacted with
133 ned to generate thermodynamically disfavored alkenyl chlorides and fluorides in high yield and with e
134 vides access to a broad array of substituted alkenyl chlorides in excellent yields and with high regi
137 SalG has broad substrate tolerance toward 2-alkenyl-CoAs that give rise to the salinosporamide C-2 s
138 ytically active chiral NHC-Cu-aryl or NHC-Cu-alkenyl complex can be accessed from reaction of a Cu-ha
140 sopropoxy substituents (>99:1), whereas most alkenyl complexes give high selectivity with both substi
143 hat NHCCuOTf rapidly traps NHCCuX (X = F, H, alkenyl) complexes to produce (NHCCu)2(mu-X)(OTf) (X = F
145 ethod was developed for the hydroboration of alkenyl-containing organotrifluoroborates to generate di
148 the structure, stability, and reactivity of alkenyl copper intermediates, as well as insight into th
150 rectly couple di-, tri- and tetrasubstituted alkenyl cyanohydrin pronucleophiles to prepare the corre
151 Fe-mediated cyclocarbonylation of a derived alkenyl cyclopropane gave a bicyclic enone that then was
152 ion in the presence of Fe(CO)5 converted the alkenyl cyclopropanes to the 2-substituted cyclohexenone
155 l group on the nitrogen atom of the tethered alkenyl diazo amido indolo ester seemingly provides bett
156 They are also linked by the A rings by an alkenyl diester bridge to restrict the conformational fl
157 s-coupling processes had used either aryl or alkenyl electrophiles as one of the coupling partners.
158 ables the stereoselective formation of O-(Z)-alkenyl ether as precursors for the synthesis of plasmen
163 (RCM) was employed to join carboxy-terminal alkenyl glycine side chains together with vinyl- and all
164 followed by cross-coupling of the resulting alkenyl Grignard reagent with aryl halide to give tetras
166 For cyclopropanes bearing a trisubstituted alkenyl group either the corresponding cyclopent-3-enes
173 of the initial structural identities of the alkenyl groups are attributable to the formation of ally
174 tions permit installation of a wide range of alkenyl groups at positions beta, gamma, or delta to a c
175 Substrates having gem-hydrogen, -alkyl, or -alkenyl groups give products with stereochemical retenti
176 yl-, acyclic, or heterocyclic trisubstituted alkenyl groups may be added in up to >98% yield, >98:2 S
177 tho-alkylation of aromatic imines containing alkenyl groups tethered at the meta position relative to
178 the first solution to the problem of ECA of alkenyl groups to acyclic trisubstituted enones, an adva
182 nd Pd-catalyzed cross-coupling with aryl and alkenyl halides proceeded smoothly with essentially comp
183 ziridinyl stannatrane 8 couples with aryl or alkenyl halides RX under modified Stille conditions to a
185 an aryl bromide, an activated aryl chloride, alkenyl halides, and an alkynyl bromide) serve as suitab
186 place of alkynes to furnish tetrasubstituted alkenyl halides, showcasing the first halo-arylation of
187 with a number of functional groups including alkenyl halides, sulfides, triflates, and phosphonates a
192 )2 in the oxidation of a series of alkyl and alkenyl hydrocarbons as well as of an aromatic sulfide w
196 urally complex Z-alkenyl-B(pin) as well as Z-alkenyl iodide compounds reliably, efficiently, and with
201 2) complexes 1a-c and 2a-c and five types of alkenyl iodides A-E were chosen for the study, thereby d
202 sed cross-coupling reaction uniting the core alkenyl iodides and the side-chain alkenylsilanol was ac
203 s described, in which ortho-acylanilines and alkenyl iodides converted to multisubstituted quinolines
205 pyrroles in good to excellent yields, while alkenyl iodides provide the corresponding acyl pyrroles
206 ws the direct conjugate addition of aryl and alkenyl iodides, bromides, and to a lesser extent, chlor
207 ert the cyclization product to both E- and Z-alkenyl iodides, which would eventually lead to isodomoi
209 2 + 2] cycloaddition of terminal alkynes and alkenyl isocyanates leading to the formation of indolizi
210 The first conjugate addition/alkylation to alkenyl isocyanides is described, which addresses this d
211 ta- and beta,beta-disubstituted arylsulfonyl alkenyl isocyanides to rapidly assemble diverse isocyani
212 is bonded to the osmium atom and a bridging alkenyl ligand that is pi-bonded to the osmium atom.
213 Compounds 12 and 13 are isomers containing alkenyl ligands formed by the insertion of the PhC2H mol
214 3T cells significantly decreased LPEAT and 1-alkenyl-LPEAT activities but did not affect other lysoph
215 ependent acyltransferase activity toward 1-O-alkenyl-lysophosphatidylethanolamine, lysophosphatidylgl
216 yntheses of natural and unnatural conjugated alkenyl(methyl)maleic anhydrides have been described.
217 ic alcohols were transformed into conjugated alkenyl(methyl)maleic anhydrides via oxidation followed
219 xtradiol catechol dioxygenases: a direct 1,2-alkenyl migration for extradiol cleavage and an O-O homo
222 bile molecule of water and an iridium-bonded alkenyl moiety (-C(R) horizontal lineC(R)-(R=CO2Me)) as
223 donor-acceptor cyclopropanes, containing an alkenyl moiety and diverse electron-withdrawing group(s)
224 the cleavage of the terminal C-H bond of the alkenyl moiety and the dearomatization of the phenol rin
226 (SuFEx) click chemistry, in which either the alkenyl moiety or the sulfonyl fluoride group can be the
227 the cleavage of the terminal C-H bond of the alkenyl moiety, generates highly valuable benzoxepine sk
228 d to proceed with the assistance of an ortho-alkenyl moiety, which is formed by the initial alkyne co
231 Both aromatic and aliphatic gamma- and delta-alkenyl N-arylsulfonamides undergo the oxidative cycliza
233 o rotation around the N-alkenyl bond of 38 N-alkenyl-N-alkylacetamide derivatives was measured (Delta
234 The radical cyclizations of a subset of N-alkenyl-N-benzyl-alpha-haloacetamides exhibiting relativ
236 h (Z)-alkenyl pinacol boronic esters and (E)-alkenyl neopentyl boronic esters gave (E)-syn- and (E)-a
237 of the dimers, byproducts formed through the alkenyl Ni species, are observed; (3) the coupling goes
238 ype reactions generate valuable (hetero)aryl/alkenyl nitriles, iodides, and bromides as well as allyl
240 tterns, along with a wide range of boron and alkenyl nucleophiles that couple under palladium catalys
242 ty and very high regioselectivities, placing alkenyl or alkynyl groups distal to the forming C-C bond
243 cts with up to 94% ee from readily available alkenyl or aryl bromides and N-boc-pent-4-enylamines.
246 ocks for the preparation of functionalized 3-alkenyl-oxindoles through a Suzuki-Miyaura reaction.
247 tem, presumably via the in situ formation of alkenyl-oxocarbenium intermediates, which eliminates the
248 this method is expanded by the generation of alkenyl-oxocarbenium species as highly activated alkene
251 tive with other methods for the synthesis of alkenyl phosphorus compounds, and in the case of trisubs
252 e in which the HMBPP product forms an eta(2)-alkenyl pi- (or pi/sigma) complex with the 4th Fe in the
253 eine-complexed lithiated carbamates with (Z)-alkenyl pinacol boronic esters and (E)-alkenyl neopentyl
254 Reactions can involve a variety of robust alkenyl-(pinacolatoboron) [alkenyl-B(pin)] compounds tha
255 re then stereoselectively reduced to the cis-alkenyl pinacolboronates via hydroboration with dicycloh
256 , and leading to cyclic ketones featuring an alkenyl side chain with complete diastereoselectivity.
257 avoring formation of 2,2-disubstituted metal-alkenyl species and subsequently the Markovnikov vinyl s
259 s, carbamates, and thiocarbamates bearing N'-alkenyl substituents generates carbanions which undergo
260 tiomerically pure 2-pyrones, or converted to alkenyl-substituted 2-pyrones such as naturally occurrin
262 promoting the [2+2] photocycloaddition of 4-alkenyl-substituted coumarins, which led to the correspo
263 unctionalization at the C(2)-position of a N-alkenyl-substituted indole derivative that was also stud
266 s, we identified a new class of alkynyl- and alkenyl-substituted macrolides with activities comparabl
268 Similar reactions were accomplished with an alkenyl-substituted pyrimidine, pyrazine, thiazole, quin
269 e (NBD) readily generate the bicyclic alkyl-/alkenyl-substituted stannylenes, ArSn(norbornyl) (2a or
270 corresponding aryl-, heteroaryl-, alkyl-, or alkenyl-substituted terminal alkynes with diisobutylalum
274 Studies with geometrically pure E- and Z-alkenyl sulfide isomers reveal a likely dichotomy of rea
276 ed by either (a) a cyclization cascade of an alkenyl sulfide tethered to a 2-azido-1-allenylbenzene c
277 re or (b) cationic cyclization of a tethered alkenyl sulfide with a putative 2-indolidenium cation.
279 uning the stereoelectronic properties of the alkenyl sulfides intermediates in order to improve the d
281 intramolecular cyclocondensation of tethered alkenyl sulfides with either indolidene or indolidenium
282 ifluoroborates with a variety of substituted alkenyl sulfones through an alpha-aminomethyl radical ad
283 proteins and small molecules yielding stable alkenyl sulfoxide products at rates more than 100x great
284 -alkyl, N-allyl-, and N-benzyl-substituted S-alkenyl sulfoximines under appropriate conditions result
290 e reaction is general for a broad range of 4-alkenyl triazoles and dienes, enabling the stereoselecti
292 tioselective intermolecular Heck reaction of alkenyl triflates and acyclic primary or racemic seconda
293 utilize a redox-relay Heck reaction between alkenyl triflates and acyclic trisubstituted alkenols of
295 The new process forms highly substituted alkenyl triflates from a range of alkynes via a pathway
296 ttributed to the use of electron-withdrawing alkenyl triflates, which offer selective beta-hydride el
297 (EAS) reactions that allow for additions of alkenyl units to readily accessible allylic electrophile
298 s from the corresponding starting E- or Z-N'-alkenyl urea, each of which may be formed from the same
299 ations of a number of terminally unsaturated alkenyl zinc iodides to cyclopentylmethylzinc iodides, f
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