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Xibin Gu et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 9(3), 350-369 (2008-02-16)
During the last decade, experimental and theoretical studies on the unimolecular decomposition of cumulenes (H(2)C(n)H(2)) from propadiene (H(2)CCCH(2)) to hexapentaene (H(2)CCCCCCH(2)) have received considerable attention due to the importance of these carbon-bearing molecules in combustion flames, chemical vapor deposition processes
Nozomi Saito et al.
Chemistry, an Asian journal, 7(7), 1521-1523 (2012-04-25)
Three's not a crowd: An intramolecular [2+2+2] cyclization between three different components, allene, alkyne, and alkene, has been realized using a catalytic amount of [Cp*RuCl(cod)] complex (cod = 1,5-cyclooctadiene), and afforded fused-tricyclic compounds in a highly stereoselective manner.
Synthetic applications of intramolecular enone-olefin photocycloadditions.
Crimmins M T
Chemical Reviews, 88(8), 1453-1473 (1988)
Inmaculada R Lahoz et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(43), 13836-13843 (2012-09-13)
New 2,6-disubstituted pyrido-allenophanes with locked rotation of aromatic spacers were designed and synthesized. The synthesis was accomplished by Pd-catalyzed C(sp(2))-C(sp) Sonogashira cross-coupling reaction between 1,3-diethynylallene (DEA) and 2,6-dibromopyridine followed by an intermolecular ring closure. Because racemic DEA was employed, pyrido-allenophanes
Hood Thabit et al.
Lancet (London, England), 385 Suppl 1, S96-S96 (2015-08-28)
The closed-loop system (artificial pancreas) delivers insulin in a glucose-responsive manner by the use of a control algorithm that automatically directs insulin delivery, based on real-time sensor glucose concentrations. Results from hospital-based studies have shown improved overnight glucose control and
Anna On-Yee Chan et al.
Chemical communications (Cambridge, England), 49(14), 1428-1430 (2013-01-17)
A new approach for selective modification of cysteine-containing peptides through gold-mediated oxidative allene-thiol coupling reaction in aqueous medium is developed.
Versatile allene and carbon dioxide equivalents for the Diels-Alder reaction.
Bonjouklian R and Ruden R A
The Journal of Organic Chemistry, 42(25), 4095-4103 (1977)
Fuyuhiko Inagaki et al.
Chemical & pharmaceutical bulletin, 60(3), 381-384 (2012-03-03)
The regioselective intramolecular 1,3-dipolar cycloaddition of the phenylsulfonylallene-nitrone derivatives has been developed. This reaction showed that the distal double bond of the allene exclusively reacted with the nitrone group to produce the bicyclic isoxazolidine derivatives regardless of the substitution pattern
Suyu Huang et al.
Chemical communications (Cambridge, England), 48(16), 2204-2206 (2012-01-19)
A Rh-catalyzed 1,3-acyloxy migration of propargyl ester followed by intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne was developed. This tandem reaction provides access to bicyclic compounds containing a highly functionalized isotoluene or cyclohexenone structural motif, while only aromatic compounds
Allene.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2007)
Simple route to mono-, di-, and tri-substituted allenic compounds.
Linstrumelle G and Michelot D
Journal of the Chemical Society. Chemical Communications, 14, 561-562 (1975)
Baoqiang Wan et al.
Angewandte Chemie (International ed. in English), 52(1), 441-445 (2012-09-11)
Getting axed: synthesis of the title amines, bearing functionality (R(1) and R(2)), involves the enantioselective palladium-catalyzed decarboxylation of allenyl N-tosylcarbamates. The reaction proceeds smoothly using both the chiral ligands (S)- and (R)-DTBM-Segphos (1) to afford the allenyl amines in good
Anthony Pitaval et al.
Organic letters, 15(17), 4580-4583 (2013-08-22)
Gold(I)-catalyzed allene-vinylcyclopropane cycloisomerization leads to the tricyclic framework of the protoilludanes in a single step by a reaction that involves a cyclopropane ring expansion and a Prins cyclization.
Fanke Meng et al.
Organic letters, 15(6), 1414-1417 (2013-03-07)
Two types of NHC-Cu complexes catalyze protoborations of terminal allenes to afford valuable 1,1- or trisubstituted vinylboron species with high site selectivity and stereoselectivity. The scope of the method, application to natural product synthesis, and mechanistic basis for the observed
Harry A Dailey et al.
Proceedings of the National Academy of Sciences of the United States of America, 112(7), 2210-2215 (2015-02-04)
It has been generally accepted that biosynthesis of protoheme (heme) uses a common set of core metabolic intermediates that includes protoporphyrin. Herein, we show that the Actinobacteria and Firmicutes (high-GC and low-GC Gram-positive bacteria) are unable to synthesize protoporphyrin. Instead
?-Cyanocyclobutenone as a highly reactive dienophile in comparison to ?-cyanocyclopentenone.
Bienfait B, et al.
Tetrahedron, 47(38), 8167-8176 (1991)
Juan Muñoz-Bascón et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(45), 14479-14486 (2012-09-22)
The alkyne functional group is found in many bioactive natural products and is the key to many important chemical transformations developed over recent years. Moreover, allenes have recently gained relevance as versatile reagents in organic synthesis. Mild, catalytic methods to
Valerian Gobé et al.
Organic letters, 16(7), 1924-1927 (2014-03-26)
The pallado-catalyzed tandem deprotection/cyclization reaction of enantioenriched N-allyl tetrahydro-β-carbolines on allenes is described. The first step generates in situ a deprotected tetrahydro-β-carboline, which then undergoes a cyclization on the allene function via an intermediate π-allyl Pd(II) derivative. This reaction results
Cale D Weatherly et al.
Organic letters, 14(7), 1704-1707 (2012-03-22)
The synthesis of 1,3-diaminated stereotriads via the bis-aziridination of allenes is reported. The reactive 1,4-diazaspiro[2.2]pentane intermediates undergo a mild Brønsted acid-promoted rearrangement to yield 1,3-diaminated ketones in good yields with excellent stereocontrol. Directed reduction of the ketone can be achieved
Shinji Kitagaki et al.
Organic letters, 14(6), 1366-1369 (2012-03-01)
The thermal reaction of 1,4-bisallenes with the aid of Cu salt/amine significantly suppressed the formal [3,3] sigmatropic rearrangement resulting in the highly selective formation of the bicyclo[4.2.0]octadiene framework. This reaction could be applied to the one-pot synthesis of bicyclo[4.2.0]octadienes from
Jiajia Cheng et al.
Chemical communications (Cambridge, England), 48(99), 12074-12076 (2012-11-09)
FeCl(3)-catalyzed aza-Prins-cyclization reaction of α-sulfonamido-allenes with aldehydes afforded 1,2,3,6-tetrahydropyridine or 2,5-dihydro-1H-pyrrole derivatives efficiently and highly selectively. The different regioselectivity is probably caused by the stabilizing effect of the phenyl group on the positively charged allylic intermediate.
Gold(I)-catalyzed stereoconvergent, intermolecular enantioselective hydroamination of allenes.
Kristina L Butler et al.
Angewandte Chemie (International ed. in English), 51(21), 5175-5178 (2012-04-12)
The silyl-cupration and stannyl-cupration of allenes.
Fleming I, et al.
Tetrahedron, 45(2), 413-424 (1989)
Guosheng Liu
Organic & biomolecular chemistry, 10(31), 6243-6248 (2012-06-27)
Transition metal catalysts have been developed for introducing fluorine into organic compounds. Recent progress in this area is reviewed with an emphasis on the selective fluorination of alkenes, alkynes and allenes. Regio- and stereoselective fluorination reactions are highlighted.
Ersan Tatli et al.
Journal of interventional cardiology, 28(3), 305-312 (2015-05-21)
We aimed to present our experience regarding the unusual vascular complications and specific treatment strategies in patients who underwent transradial coronary procedure (TRC). Transradial access provides lower vascular access site complication rates compared with transfemoral access. However, there is lack
Wu Fan et al.
Angewandte Chemie (International ed. in English), 53(52), 14542-14545 (2014-10-30)
A novel copper(I)-catalyzed three-component reaction for the efficient synthesis of 3-amino-2-pyrones and 2,5-dihydrofurans from propargyl alcohols, aldehydes, and amines has been developed. The starting materials are easily available and the scope of this method is broad. Through mechanistic studies, it
Keith R Fandrick et al.
Organic letters, 15(6), 1214-1217 (2013-02-27)
A practical and highly site-selective copper-PhBPE-catalyst-controlled allenylation with propargyl boronates has been developed. The methodology has shown to be tolerant of diverse ketones and aldehydes providing the allenyl adducts in high selectivity. The BPE ligand and boronate substituents were shown
Iodine-initiated domino reaction of hepta-1,2-dien-6-yn-4-ols and Brønsted acid promoted cyclization of hepta-1,2,6-trien-4-ols leading to functionalized benzenes.
Yan He et al.
Chemistry, an Asian journal, 8(4), 717-722 (2013-01-23)
Hiyun Kim et al.
Current opinion in drug discovery & development, 11(6), 870-894 (2008-10-24)
Presented is a review of the advances in synthetic methodology that make use of the allene functional group, with emphasis on catalytic asymmetric transformations and new mechanistic insights. The review covers the period from January 2007 to May 2008 and
Chung-Yeh Wu et al.
Nature, 517(7535), 449-454 (2015-01-23)
Low-valent late transition-metal catalysis has become indispensable to chemical synthesis, but homogeneous high-valent transition-metal catalysis is underdeveloped, mainly owing to the reactivity of high-valent transition-metal complexes and the challenges associated with synthesizing them. Here we report a carbon-carbon bond cleavage
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