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1.
Hai‐Hua Lu Hui Liu Dr. Wei Wu Xu‐Fan Wang Liang‐Qiu Lu Wen‐Jing Xiao Prof. Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(12):2742-2746
Economical approach : The first organocatalytic asymmetric intramolecular hydroarylation of phenol‐ and aniline‐derived enals offers one of the most straightforward and atom‐economic approaches to enantioriched chromans and tetrahydroquinolines (up to 96 % ee; see scheme).
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A convenient route with high stereo control to γ‐acetoxy dienoates is provided by the reaction of methyl propiolate with aldehydes in the presence of ZnEt2 and N‐methylimidazole at room temperature, followed by the catalytic conversion of the resulting γ‐hydroxy‐α,β‐acetylenic esters with p‐N,N‐dimethylaminopyridine (DMAP) in acetic anhydride (see scheme).
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Toshihide Maki Dr. Shinya Iikawa Gen Mogami Hitomi Harasawa Yoshihiro Matsumura Prof. Dr. Osamu Onomura Prof. Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(21):5364-5370
Get selective! A selective oxidation of 1,2‐diols to α‐hydroxyketones catalyzed by organotin compounds has been developed (see scheme). Invaluable chemo‐ and stereoselectivity were found in the reaction. The catalytic system has been achieved by electrochemical and chemical oxidation.
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Qiufeng Huang Dr. Ruimao Hua Prof. Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(15):3817-3822
Economical atoms : 2‐Cyclopenten‐1‐ones, 5‐alkylidenefuran‐2(5 H)‐ones and indan‐1‐ones have been synthesized by atom‐economic reductive cyclocarbonylation of internal alkynes with carbon monoxide catalyzed by [{RhCl(CO)2}2]/CO(NH2)2 in the presence of water (see scheme).
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Jun Shi Hiroki Shigehisa Dr. Carlos A. Guerrero Ryan A. Shenvi Chuang‐Chuang Li Dr. Phil S. Baran Prof. 《Angewandte Chemie (International ed. in English)》2009,48(24):4328-4331
One stereocenter makes all the difference : The synthesis and biological evaluation of 17‐epi‐cortistatin A is reported from a common intermediate used to procure natural cortistatin A. The synthesis features a unique stereocontrolled Raney‐Ni reduction process that can be employed to reliably produce both α‐ and β‐configured D‐ring aryl steroids. Biological evaluations of these “cortalogs” are reported for the first time.
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Robert Wolf Dr. J. Chris Slootweg Dr. Andreas W. Ehlers Dr. František Hartl Dr. Bas de Bruin Dr. Martin Lutz Dr. Anthony L. Spek Prof. Dr. Koop Lammertsma Prof. Dr. 《Angewandte Chemie (International ed. in English)》2009,48(17):3104-3107
P makes it possible : The convenient oxidative synthesis of the 16‐electron organophosphorus iron sandwich complex [Fe(η4‐P2C2tBu2)2] (see structure) suggests that the elusive all‐carbon complex [Fe(η4‐C4H4)2] is a viable synthetic target.
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Zhiyong Jiang Dr. Yuanyong Yang Yuanhang Pan Yujun Zhao Hongjun Liu Choon‐Hong Tan Prof. Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(19):4925-4930
Constructing α‐stereogenic amides and ketones : The highly regioselective and enantioselective conjugate addition of 1,3‐dicarbonyl compounds to 1,4‐dicarbonyl but‐2‐enes has been developed with the chiral bicyclic guanidine as catalyst (ee values up to 97 %; see scheme).
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Hiromitsu Maeda Prof. Dr. Yoshihiro Ito Yohei Haketa Nazuki Eifuku Eunji Lee Myongsoo Lee Prof. Dr. Takeshi Hashishin Dr. Kenji Kaneko Prof. Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(15):3706-3719
Just subtract water : Amphiphilic π‐conjugated acyclic oligopyrroles form solvent‐assisted H‐aggregates that give rise to vesicular structures in aqueous solution (see figure). The H‐aggregates are sensitive to the conditions and are transformed into J‐aggregates by the removal of water.
10.
Benito Alcaide Prof. Dr. Pedro Almendros Dr. Teresa Martínez del Campo Dipl.‐Chem. M. Teresa Quirós Dipl.‐Chem. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(14):3344-3346
First insights into the reaction between a Baylis–Hillman adduct and an allene moiety have been obtained from the novel domino heterocyclization/cross‐coupling reaction of α‐allenols and Baylis–Hillman acetates, which furnishes [(2,5‐dihydrofuran‐3‐yl)methyl]acrylate derivatives in moderate to good yields.
11.
Keith A. Stubbs Dr. Matthew S. Macauley David J. Vocadlo Prof. 《Angewandte Chemie (International ed. in English)》2009,48(7):1300-1303
Gal‐PUGNAc (see picture), a highly selective inhibitor for β‐hexosaminidases HEXA and HEXB is cell‐permeable and modulates the activity of HEXA and HEXB in tissue culture, increasing ganglioside GM2 levels. Gal‐PUGNAc should allow the role of these enzymes to be studied at the cellular level without generating a complex chemical phenotype from concomitant inhibition of O‐GlcNAcase.
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Yoshihiro Matano Prof. Dr. Makoto Nakashima Hiroshi Imahori Prof. Dr. 《Angewandte Chemie (International ed. in English)》2009,48(22):4002-4005
Mind the (narrow) gap : α‐Ethynylphospholes generated in situ from the corresponding silyl‐capped precursors were converted into a series of α‐(arylethynyl) phospholes bearing functional substituents as well as an α,α′‐linked terphosphole (see scheme). The terphosphole has a narrow HOMO–LUMO gap owing to efficient π conjugation over the three phosphole rings.
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Patrick J. M. Stals Maarten M. J. Smulders Rafael Martín‐Rapún Dr. Anja R. A. Palmans Dr. E. W. Meijer Prof. Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(9):2071-2080
Molecular organization : Chiral benzene tricarboxamides with methyl substituents at defined positions self‐assemble into supramolecular polymers of preferred helicity by three‐fold α‐helical‐type hydrogen bonding. The odd–even effect is operative and all derivatives are liquid crystalline showing a Colho phase (see figure).
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Benito Alcaide Prof. Dr. Pedro Almendros Dr. Teresa Martínez del Campo Elena Soriano Dr. José L. Marco‐Contelles Prof. Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(8):1909-1928
Calculating cyclization : Theoretical work directed towards the elucidation of the mechanisms of the gold‐, palladium‐, and lanthanum‐catalyzed oxycyclizations (5‐exo versus 6‐endo versus 7‐endo) of γ‐allenols has been pursued in close relationship with the experimental study (Part 1, accompanying paper) and has corroborated the bench results to provide a complete study of the reactivity of γ‐allenols under different metal‐catalyzed conditions.
17.
Romas Kudirka Sean K. J. Devine Christopher S. Adams David L. Van Vranken Prof. 《Angewandte Chemie (International ed. in English)》2009,48(20):3677-3680
As easy as 1, 2, 3 : A palladium‐catalyzed three‐component coupling generates α,β‐unsaturated γ‐amino acids in a single step (see scheme). The reaction is believed to involve migration of a vinyl substituent to a highly electrophilic palladium carbene. Unlike previous synthetic approaches, this synthesis provides access to γ‐amino acids with non‐natural side chains.
18.
Jie Han Dr. Xiao‐Yong Chang Li‐Rong Zhu Mei‐Li Pang Dr. Ji‐Ben Meng Prof. Stephen Sin‐Yin Chui Dr. Siu‐Wai Lai Dr. V. A. L. Roy Dr. 《化学:亚洲杂志》2009,4(7):1099-1107
Chain change : Variations in the position, number, and chain length of the n‐alkoxy chains readily tune the liquid‐crystalline properties of 2,5‐diaryl‐1,3,4‐thiadiazole derivatives from smectic to hexagonal columnar mesophases at room temperature. The calamitic S‐heterocyclic compounds show electrical conductivity in both solid and liquid‐crystal states.
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Massimo Stefanoni Marco Luparia Dr. Alessio Porta Dr. Giuseppe Zanoni Dr. Giovanni Vidari Prof. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(16):3940-3944
Rhenium does the job! A readily available rhenium complex efficiently catalyzed the direct Meyer–Schuster‐like rearrangement of different alkyl‐ and aryl‐substituted propargylic secondary and tertiary alcohols to the corresponding α,β‐unsaturated compounds, which were produced with virtually complete E stereoselectivity. The reaction proceeded under neutral conditions and no racemization of potentially enolizable stereocenters was observed.