Masahiro Terada

Summary

Affiliation: Tohoku University
Country: Japan

Publications

  1. ncbi request reprint Axially chiral guanidine as enantioselective base catalyst for 1,4-addition reaction of 1,3-dicarbonyl compounds with conjugated nitroalkenes
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    J Am Chem Soc 128:1454-5. 2006
  2. ncbi request reprint Axially chiral guanidine as highly active and enantioselective catalyst for electrophilic amination of unsymmetrically substituted 1,3-dicarbonyl compounds
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    J Am Chem Soc 128:16044-5. 2006
  3. ncbi request reprint Enantioselective 1,4-addition reactions of diphenyl phosphite to nitroalkenes catalyzed by an axially chiral guanidine
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    J Am Chem Soc 129:14112-3. 2007
  4. ncbi request reprint Enantioselective direct aldol-type reaction of azlactone via protonation of vinyl ethers by a chiral Brønsted acid catalyst
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    J Am Chem Soc 131:3430-1. 2009
  5. doi request reprint Enantioselective direct vinylogous Michael addition of functionalized furanones to nitroalkenes catalyzed by an axially chiral guanidine base
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    Org Lett 13:2026-9. 2011
  6. doi request reprint Enantioselective Henry (nitroaldol) reaction catalyzed by axially chiral guanidines
    Hitoshi Ube
    Department of Chemistry, Graduate School of Science, Tohoku University, Aoba ku, Sendai, Japan
    Bioorg Med Chem Lett 19:3895-8. 2009
  7. doi request reprint Chiral Brønsted acid catalyzed stereoselective addition of azlactones to 3-vinylindoles for facile access to enantioenriched tryptophan derivatives
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba ku, Sendai 980 8578, Japan
    Angew Chem Int Ed Engl 50:12586-90. 2011
  8. ncbi request reprint Enantioselective friedel-crafts reaction of electron-rich alkenes catalyzed by chiral Brønsted acid
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    J Am Chem Soc 129:292-3. 2007
  9. ncbi request reprint Platinum-catalyzed dehydroalkoxylation-cyclization cascade via N-O bond cleavage
    Itaru Nakamura
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    J Am Chem Soc 131:4198-9. 2009
  10. ncbi request reprint Copper-catalyzed rearrangement of (Z)-propynal hydrazones via N-N bond cleavage
    Itaru Nakamura
    Research and Analytical Center for Giant Molecules and Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578 Japan
    Org Lett 12:4198-200. 2010

Collaborators

Detail Information

Publications26

  1. ncbi request reprint Axially chiral guanidine as enantioselective base catalyst for 1,4-addition reaction of 1,3-dicarbonyl compounds with conjugated nitroalkenes
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    J Am Chem Soc 128:1454-5. 2006
    ..The axially chiral guanidine catalysts thus developed facilitated the highly enantioselective 1,4-addition reaction of 1,3-dicarbonyl compounds with a broad range of conjugated nitroalkenes and showed extremely high catalytic activity...
  2. ncbi request reprint Axially chiral guanidine as highly active and enantioselective catalyst for electrophilic amination of unsymmetrically substituted 1,3-dicarbonyl compounds
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    J Am Chem Soc 128:16044-5. 2006
    ....
  3. ncbi request reprint Enantioselective 1,4-addition reactions of diphenyl phosphite to nitroalkenes catalyzed by an axially chiral guanidine
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    J Am Chem Soc 129:14112-3. 2007
  4. ncbi request reprint Enantioselective direct aldol-type reaction of azlactone via protonation of vinyl ethers by a chiral Brønsted acid catalyst
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    J Am Chem Soc 131:3430-1. 2009
    ..The method provides efficient access to biologically and pharmaceutically intriguing beta-hydroxy-alpha-amino acid derivatives having a quaternary stereogenic center at the alpha-carbon atom...
  5. doi request reprint Enantioselective direct vinylogous Michael addition of functionalized furanones to nitroalkenes catalyzed by an axially chiral guanidine base
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    Org Lett 13:2026-9. 2011
    ..The method provides facile access to enantioenriched α,γ-functionalized butenolides that can be further manipulated, thereby rendering them useful synthetic intermediates...
  6. doi request reprint Enantioselective Henry (nitroaldol) reaction catalyzed by axially chiral guanidines
    Hitoshi Ube
    Department of Chemistry, Graduate School of Science, Tohoku University, Aoba ku, Sendai, Japan
    Bioorg Med Chem Lett 19:3895-8. 2009
    ..Optically active nitroaldol products were obtained in acceptable yields with fairly good enantio- and diastereoselectivities at low temperature...
  7. doi request reprint Chiral Brønsted acid catalyzed stereoselective addition of azlactones to 3-vinylindoles for facile access to enantioenriched tryptophan derivatives
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba ku, Sendai 980 8578, Japan
    Angew Chem Int Ed Engl 50:12586-90. 2011
    ..This method enables facile access to tryptophan derivatives with adjacent quaternary and tertiary stereogenic centers, which are potentially useful for the synthesis of peptidomimetics...
  8. ncbi request reprint Enantioselective friedel-crafts reaction of electron-rich alkenes catalyzed by chiral Brønsted acid
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    J Am Chem Soc 129:292-3. 2007
  9. ncbi request reprint Platinum-catalyzed dehydroalkoxylation-cyclization cascade via N-O bond cleavage
    Itaru Nakamura
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    J Am Chem Soc 131:4198-9. 2009
    ....
  10. ncbi request reprint Copper-catalyzed rearrangement of (Z)-propynal hydrazones via N-N bond cleavage
    Itaru Nakamura
    Research and Analytical Center for Giant Molecules and Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578 Japan
    Org Lett 12:4198-200. 2010
    ....
  11. ncbi request reprint Chiral Brønsted acid catalysis for enantioselective Hosomi-Sakurai reaction of imines with allyltrimethylsilane
    Norie Momiyama
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 980 8578, Japan
    Org Lett 13:2126-9. 2011
    ....
  12. ncbi request reprint Palladium-catalyzed indolization of N-aroylbenzotriazoles with disubstituted alkynes
    Itaru Nakamura
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    Org Lett 11:1055-8. 2009
    ..In the present reaction, the aroylbenzotriazole acts as a synthetic equivalent of a 2-haloanilide in Larock's indole synthesis...
  13. doi request reprint Oxazepine synthesis by copper-catalyzed intermolecular cascade reactions between O-propargylic oximes and dipolarophiles
    Itaru Nakamura
    Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai, 980 8578, Japan
    Angew Chem Int Ed Engl 52:7536-9. 2013
    ..The process involves the cleavage of C- and N-O bonds...
  14. doi request reprint Double bond isomerization/enantioselective aza-Petasis-Ferrier rearrangement sequence as an efficient entry to anti- and enantioenriched beta-amino aldehydes
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    J Am Chem Soc 131:6354-5. 2009
    ..The chiral phosphoric acid also functioned as an efficient resolving catalyst of racemic hemiaminal vinyl ethers...
  15. ncbi request reprint Copper-catalyzed skeletal rearrangement of O-propargylic alkylaldoximes via N-O bond cleavage
    Itaru Nakamura
    Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    Org Lett 14:206-9. 2012
    ..O-Propargylic oximes that possess a proton at the α-position of the oxime group were effectively converted to the corresponding oxiranyl N-alkenylimines via a 5-endo-dig cyclization followed by the cleavage of the N-O bond...
  16. ncbi request reprint Mechanistic studies of highly enantio- and diastereoselective aza-Petasis-Ferrier rearrangement catalyzed by chiral phosphoric acid
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Aoba ku, Sendai 980 8578, Japan
    J Am Chem Soc 136:7044-57. 2014
    ..The results of experiments and theoretical studies fully support the proposed mechanism of the present anti- and enantioselective APF rearrangement. ..
  17. ncbi request reprint Cu-catalyzed skeletal rearrangement of o-propargylic electron-rich arylaldoximes into amidodienes
    Itaru Nakamura
    Research and Analytical Center for Giant Molecules and Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    Org Lett 16:2562-5. 2014
    ..The reaction proceeded via a 2,3-rearrangement, followed by isomerization of the resulting N-allenylnitrone to the amide, presumably through the oxaziridine intermediate. ..
  18. ncbi request reprint Intramolecular Cyclization of Alkynyl α-Ketoanilide Utilizing [1,2]-Phospha-Brook Rearrangement Catalyzed by Phosphazene Base
    Azusa Kondoh
    Department of Chemistry and Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aoba ku, Sendai 980 8578, Japan
    Org Lett 16:3528-31. 2014
    ..Under high-temperature reaction conditions, further rearrangement of the allylic phosphate moiety occurs to provide 2-quinolone derivatives. ..
  19. ncbi request reprint Chiral silver phosphate catalyzed transformation of ortho-alkynylaryl ketones into 1H-isochromene derivatives through an intramolecular-cyclization/enantioselective-reduction sequence
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba ku, Sendai 980 8578 Japan http www orgreact sakura ne jp index html Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aramaki, Aoba ku, Sendai 980 8578 Japan
    Angew Chem Int Ed Engl 53:235-9. 2014
    ..An asymmetric synthesis of the 9-oxabicyclo[3.3.1]nona-2,6-diene framework, which has been found in some biologically active molecules, is presented as a demonstration of the synthetic utility of this method. ..
  20. doi request reprint Phosphazene-catalyzed intramolecular cyclization of nitrogen-tethered alkynyl esters
    Azusa Kondoh
    Department of Chemistry, Graduate School of Science, Tohoku University, Aoba ku, Sendai 980 8578, Japan
    Chem Commun (Camb) 49:10254-6. 2013
    ..Both acyclic and cyclic substrates underwent 5-exo-dig and 5-endo-dig cyclization. This reaction is a rare example of the intramolecular addition of enolates of simple esters to alkynes. ..
  21. doi request reprint Chiral anion catalysis in the enantioselective 1,4-reduction of the 1-benzopyrylium ion as a reactive intermediate
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba ku, Sendai 980 8578 Japan, Fax 81 22 795 6584 Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aramaki, Aoba ku, Sendai 980 8578 Japan
    Chemistry 19:13658-62. 2013
    ....
  22. doi request reprint Synthesis of azepine derivatives by rhodium-catalyzed tandem 2,3-rearrangement/heterocyclization
    Itaru Nakamura
    Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai, 980 8578 Japan http www orgreact sakura ne jp en index html
    Angew Chem Int Ed Engl 51:10816-9. 2012
    ....
  23. ncbi request reprint Relay catalysis using a rhodium complex/chiral brønsted Acid binary system: enantioselective reduction of a carbonyl ylide as the reactive intermediate
    Masahiro Terada
    Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba ku, Sendai 980 8578 Japan http www orgreact sakura ne jp index html Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aramaki, Aoba ku, Sendai 980 8578 Japan
    Angew Chem Int Ed Engl 51:2093-7. 2012
    ..The four-step transformation involves a rhodium carbene complex, a carbonyl ylide, and an isobenzopyrylium intermediate, the enantioselective reduction of which yields isochromanone derivatives in good yield with high selectivity...
  24. ncbi request reprint Platinum-catalyzed cycloisomerization of 1,4-enynes via 1,2-alkenyl rearrangement
    Takuma Sato
    Department of Chemistry and Research, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    Org Lett 13:4992-5. 2011
    ..The reaction proceeded through an unprecedented 1,2-alkenyl rearrangement that afforded a novel reaction topology of 1,4-enynes...
  25. ncbi request reprint Activation of hemiaminal ethers by chiral brønsted acids for facile access to enantioselective two-carbon homologation using enecarbamates
    Masahiro Terada
    Department of Chemistry, Graduate School of Scienece, Tohoku University, Aramaki, Aoba ku, Sendai 980 8578 Japan, Fax 81 22 795 6602, http hanyu chem tohoku ac jp approximately web lab index2 html
    Angew Chem Int Ed Engl 48:2553-6. 2009
    ..The process affords the corresponding products in good to high enantioselectivity (see scheme; Boc=tert-butoxycarbonyl, G=aromatic group). The method enables facile access to highly enantioenriched 1,3-diamine derivatives...
  26. ncbi request reprint Regioselective transformation of O-propargylic arylaldoximes to four-membered cyclic nitrones by copper-catalyzed skeletal rearrangement
    Itaru Nakamura
    Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai 980 8578, Japan
    Org Lett 13:3616-9. 2011
    ..The reactions proceeded via a tandem [2,3]-rearrangement and 4π-electrocyclization of the N-allenylnitrone intermediate and involved cleavage of the carbon-oxygen bond...