- A helically twisted imine macrocycle that allows for determining the absolute configuration of α-amino carboxylates
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Binding of α-amino carboxylates to a helically twisted imine macrocycle based on the indolocarbazole scaffold gives rise to characteristic circular dichroism spectra, and the patterns of the Cotton effects are consistent with the absolute configuration of
- Kim, Min Jun,Choi, Ye Rin,Jeon, Hae-Geun,Kang, Philjae,Choi, Moon-Gun,Jeong, Kyu-Sung
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- Palladium-Catalyzed Aminomethylative Oppolzer-Type Cyclization of Enynes: Access to Aminomethylated Benzofulvenes
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A novel palladium-catalyzed Oppolzer-type cyclization reaction aided by the aminomethyl cyclopalladated complex has been developed, which provides rapid access to functionalized benzofulvenes with excellent stereoselectivity. The corresponding products can undergo Diels–Alder reaction with maleimides, providing a series of complex polycyclic compounds with excellent regio- and stereoselectivities.
- Huang, Hanmin,Huang, Renbin,Li, Renren,Yu, Bangkui
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supporting information
p. 9510 - 9515
(2021/12/14)
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- A Gold(I)-Catalyzed Tandem Cyclization to Benzo[b]indeno[1,2-e][1,4]diazepines from o-Phenylenediamines and Ynones
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A gold-catalyzed tandem cyclization of o-phenylenediamines with ynones to synthesize benzo[b]indeno[1,2-e][1,4]diazepine has been developed. The mechanism was explored by control experiments. The method provides a way to access a range of benzo[b]indeno[1,2-e][1,4]diazepine derivatives in diversity-oriented synthesis aiming at discovering structurally diverse scaffolds. (Figure presented.).
- Xie, Fukai,Zhang, Bo,Chen, Yanyu,Jia, Hongwei,Sun, Lei,Zhuang, Kaitong,Yin, Lili,Cheng, Maosheng,Lin, Bin,Liu, Yongxiang
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supporting information
p. 3886 - 3897
(2020/08/06)
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- Palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination: Access to functionalized naphthalenes
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A palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination of enyne-tethered allylic alcohols with aminals is described. Under the reaction conditions, the cationic vinyl allylpalladium species undergoes selective migratory insertion of alkenes rather than reductive elimination with nucleophiles. This strategy provides an efficient and unique approach to the construction of functionalized naphthalenes, which are important building blocks in synthetic organic chemistry. Mechanistic studies have revealed that the selective sequential migratory insertion of enyne and alkene is crucial for the cyclization.
- Yu, Bangkui,Yu, Houjian,Huang, Hanmin
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p. 8962 - 8966
(2020/11/13)
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- De Novo Synthesis of Phenols and Naphthols through Oxidative Cycloaromatization of Dienynes
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In this work, a rhodium-catalyzed oxidative cycloaromatization of dienynes, which provides a highly straightforward and efficient way to access polysubstituted naphthols and phenols under mild conditions, is described. Challenged electron-withdrawing groups are well tolerated in this protocol, and late-stage phenyl ring formation is demonstrated.
- Rong, Ming-Guang,Qin, Tian-Zhu,Liu, Xin-Rui,Wang, Hong-Fa,Zi, Weiwei
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supporting information
p. 6289 - 6293
(2018/10/09)
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- Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes
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1,5-Diyne systems bearing one terminal and one benzyl- or allyl-substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold-catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C(sp2)–H bond of the offered unsaturated systems. If H atoms are present in the propargylic position, a subsequent isomerization to the aromatic system takes place leading to 9H-fluorene and 11H-benzo[b]fluorene derivatives as final products. In the case of a quaternary carbon in the propargylic position no further aromatization is observed and 10H-benzo[b]fluorene derivatives are obtained in high yield. (Figure presented.).
- Bucher, Janina,Wurm, Thomas,Taschinski, Svenja,Sachs, Eleni,Ascough, David,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
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supporting information
p. 225 - 233
(2017/02/05)
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- Stereoselective Synthesis of Oxabicyclo[2.2.1]heptenes via a Tandem Dirhodium(II)-Catalyzed Triazole Denitrogenation and [3 + 2] Cycloaddition
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A novel synthetic strategy for the diastereoselective synthesis of structurally diverse oxabicyclo[2.2.1]heptenes has been developed, featuring a tandem reaction combining a Rh-catalyzed triazole denitrogenation and a novel type of [3 + 2] cycloaddition reaction. This tandem reaction was thought to proceed via a five-membered oxonium ylide intermediate, which was formed by the intramolecular nucleophilic attack of the carbonyl group on the α-imino metallocarbene followed by an inter- or intramolecular [3 + 2] dipolar cycloaddition with a range of alkynes and alkenes.
- Yuan, Hao,Gong, Jianxian,Yang, Zhen
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supporting information
p. 5500 - 5503
(2016/11/17)
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- Gold superacid-catalyzed preparation of benzo[c]thiophenes
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A three-step synthesis of benzo[c]thiophenes is presented in which the key transformation is the gold-catalyzed 5-exo-dig migratory cycloisomerization of a diallyl thioacetal. It was shown that a small amount of in situ generated HAuCl4 from AuCl3 is the active catalytic species. A mechanism was proposed.
- Debrouwer, Wouter,Seigneur, Ruben A. J.,Heugebaert, Thomas S. A.,Stevens, Christian V.
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supporting information
p. 729 - 732
(2015/01/09)
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- Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides: Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines
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Indium(III)-catalyzed cyclization reactions of aromatic 5-enynamides were studied. Indium triflate enabled the efficient synthesis of 2-aminonaphthalenes and 2-amino-1H-indenes from aromatic N-methyl-N-tosyl-ynamides bearing an ortho-vinyl and -isobutenyl group, respectively. The aromatic N-3-arylpropargylynamides bearing an ortho-gem-dihalovinyl subunit underwent a tandem cyclization/carbobromination reaction in the presence of indium tribromide to provide the dibrominated 2,3-dihydro-1H-indeno[2,1-b]pyridine derivatives in good yields.
- Yeh, Ming-Chang P.,Liang, Chia-Jung,Chen, Hsiao-Feng,Weng, Yu-Ting
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supporting information
p. 3242 - 3254
(2015/11/03)
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- Au(i)-catalyzed triple bond alkoxylation/dienolether aromaticity-driven cascade cyclization to naphthalenes
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A novel strategy for the synthesis of multisubstituted naphthalenes was developed via a Au(i)-catalyzed alkyne alkoxylation/dienolether aromaticity-driven cascade cyclization using 1,5-enyne substrates. The functional group toleration was examined by synthesizing a series of substrates and the mechanism was also studied based on intermediates isolated through deuterium labeling experiments. This journal is the Partner Organisations 2014.
- Liu, Yongxiang,Guo, Jia,Liu, Yang,Wang, Xiaoyu,Wang, Yanshi,Jia, Xinyu,Wei, Gaofei,Chen, Lizhu,Xiao, Jianyong,Cheng, Maosheng
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supporting information
p. 6243 - 6245
(2014/06/09)
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- Tunable and chemoselective syntheses of dihydroisobenzofurans and indanones via rhodium-catalyzed tandem reactions of 2-triazole-benzaldehydes and 2-triazole-alkylaryl ketones
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Two novel rhodium(II)-catalyzed tandem reactions were developed for the synthesis of dihydroisobenzofuran and indanone derivatives from 2-triazole-benzaldehydes and 2-triazole-alkylaryl ketones. Dihydroisobenzofuran derivatives were obtained in good yield
- Shen, Hongjuan,Fu, Junkai,Gong, Jianxian,Yang, Zhen
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supporting information
p. 5588 - 5591
(2015/02/19)
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- Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes
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A highly enantioselective carboalkoxylation of alkynes catalyzed by cationic (DTBM-MeO-Biphep)gold(I) complexes is reported. Various optically active β-alkoxyindanone derivatives were obtained in good yields with high enantioselectivities. Furthermore, this methodology was extended to the enantioselective synthesis of 3-methoxycyclopentenones. The reaction is proposed to proceed through an enantioselective cyclization of intermediates containing vinylgold(I) and prochiral oxocarbenium moieties.
- Zi, Weiwei,Toste, F. Dean
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supporting information
p. 12600 - 12603
(2013/09/23)
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- Gold catalysis: Catalyst oxidation state dependent dichotomy in the cyclization of furan-yne systems with aromatic tethers
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Four different synthetic strategies led to a variety of furan-yne systems that contained an aryl system in the tether. Due to the short routes to these systems (four steps or less), a small library of substrates could easily be prepared. These were treate
- Hashmi, A. Stephen K.,Hofmann, Julia,Shi, Shuai,Schuetz, Alexander,Rudolph, Matthias,Lothschuetz, Christian,Wieteck, Marcel,Buehrle, Miriam,Woelfle, Michael,Rominger, Frank
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supporting information
p. 382 - 389
(2013/02/25)
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- Synthesis of biaryl compounds using tandem ruthenium-catalyzed ring-closing metathesis
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Tandem ring-closing enyne metathesis (RCEM)/ring-closing olefin metathesis (RCM) of tetraenynes with Grubbs second-generation catalyst, followed by elimination, was found to be a new and efficient synthetic approach to biaryl compounds. A preliminary asymmetric version of this approach, which used homochiral Ru-alkylidene catalysts, is also presented. A ringing endorsement: Tandem ring-closing enyne metathesis (RCEM)/ring-closing olefin metathesis (RCM) of tetraenynes with the Grubbs second-generation catalyst followed by elimination, was found to be a new and efficient synthetic approach to biaryl compounds (see scheme). A preliminary asymmetric version of this approach is also presented.
- Yoshida, Kazuhiro,Shida, Hiroaki,Takahashi, Hidetoshi,Yanagisawa, Akira
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supporting information; experimental part
p. 344 - 349
(2011/02/27)
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- Rapid access to benzo-annelated heterocycles, naphthalenes, and polysubstituted benzenes through a novel benzannulation reaction
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A novel, efficient, and powerful methyl mercaptoacetate triggered benzannulation reaction is described. The precursors are heterocyclic, aromatic or acyclic compounds bearing a carbonyl group at ortho position to an internal alkyne. The methodology does not require transition-metal catalysts and moreover it is general for the preparation of wide range of benzo-annelated heterocycles, naphthalenes and benzenes.
- Cikotiene, Inga,Buksnaitiene, Rita,Sazinas, Rokas
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experimental part
p. 706 - 717
(2011/03/19)
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- Electronic control of product distribution in the [5+5]-coupling of ortho-alkynylbenzaldehyde derivatives and γ,δ-unsaturated carbene complexes
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The coupling of highly oxygenated ortho-alkynylbenzaldehyde derivatives with γ,δ-carbene complexes was evaluated systematically. In all of the electron-rich systems investigated the exclusive product of the reaction is the dihydrophenanthrene derivative.
- Camacho-Davila, Alejandro,Gamage, Lalith S.R.,Wang, Zhipeng,Herndon, James W.
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supporting information; experimental part
p. 4954 - 4960
(2010/08/19)
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- Efficient syntheses of α-pyridones and 3(2H)-isoquinolones through ruthenium-catalyzed cycloisomerization of 3-en-5-ynyl and o-alkynylphenyl nitrones
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We report a new catalytic synthesis of α-pyridones and 3(2H)-isoquinolones from readily available 3-en-5-ynyl nitrones and o-alkynylphenyl nitrones; the reaction mechanism is proposed to involve iminyl ketene species through an oxygen transfer process.
- Pati, Kamalkishore,Liu, Rai-Shung
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supporting information; experimental part
p. 5233 - 5235
(2010/01/31)
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- Total synthesis of antofine using the net [5+5]-cycloaddition of γ,δ-unsaturated carbene complexes and 2-alkynylphenyl ketones as a key step
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A compound containing all of the carbons of the anticancer agent antofine was produced in a single step from the coupling of a γ,δ-unsaturated carbene complex with a 2-alkynylphenyl ketone derivative. Subsequent conversion to antofine was effected in three steps.
- Camacho-Davila, Alejandro,Herndon, James W.
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p. 6682 - 6685
(2007/10/03)
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- CONDENSED HETEROAROMATIC RING SYSTEMS. XI. A FACILE SYNTHESIS OF ISOQUINOLINE N-OXIDES
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Isoquinoline 2-oxides (5a-f) were obtained by the cyclization of 2-ethynylbenzaldehyde oxime (4a-f) under basic conditions.The starting compounds (4a-f) were easily synthesized by the palladium-catalyzed reaction of 2-bromobenzaldehydes (1 and 2) with terminal acetylenes, and subsequent oximation of the resulting 2-ethynylbenzaldehydes (3a-f).
- Sakamoto, Takao,Kondo, Yoshinori,Miura, Norio,Hayashi, Kazuhiko,Yamanaka, Hiroshi
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p. 2311 - 2314
(2007/10/02)
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