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Volumn 18, Issue 9, 2006, Pages 741-745

Asymmetric aza-Henry reaction of N-tosyl imine

Author keywords

aza Henry reaction; Coordination; Diethylzinc; N tosyl imines; Nitro Mannich reaction; Reduction

Indexed keywords

CROWN COMPOUND; DIETHYLZINC; IMINE; LIGAND; N TOSYLIMINE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33748799424     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20315     Document Type: Article
Times cited : (31)

References (36)
  • 1
    • 0037434136 scopus 로고    scopus 로고
    • Asymmetric catalytic aza-Henry reactions leading to 1,2-diamines and 1,2-diaminocarboxylic acids
    • Westermann B. Asymmetric catalytic aza-Henry reactions leading to 1,2-diamines and 1,2-diaminocarboxylic acids. Angew Chem Int Ed 2003;42:151-153.
    • (2003) Angew Chem Int Ed , vol.42 , pp. 151-153
    • Westermann, B.1
  • 2
    • 12344267138 scopus 로고    scopus 로고
    • Highly enantioselective thiourea-catalyzed nitro-Mannich reactions
    • Yoon TP, Jacobsen EN. Highly enantioselective thiourea-catalyzed nitro-Mannich reactions. Angew Chem Int Ed 2005;44:466-468.
    • (2005) Angew Chem Int Ed , vol.44 , pp. 466-468
    • Yoon, T.P.1    Jacobsen, E.N.2
  • 3
    • 1342268984 scopus 로고    scopus 로고
    • Enantioselective aza-Henry reaction catalyzed by a bifunctional organocatalyst
    • Okino T, Nakamura S, Furukawa T, Takemoto Y. Enantioselective aza-Henry reaction catalyzed by a bifunctional organocatalyst Org Lett 2004;6:625-627.
    • (2004) Org Lett , vol.6 , pp. 625-627
    • Okino, T.1    Nakamura, S.2    Furukawa, T.3    Takemoto, Y.4
  • 4
    • 0033521210 scopus 로고    scopus 로고
    • The first catalytic asymmetric nitro-Mannich-type reaction promoted by a new heterobimetallic complex
    • Yamada K, Harwood SJ, Groger H, Shibasaki M. The first catalytic asymmetric nitro-Mannich-type reaction promoted by a new heterobimetallic complex. Angew Chem Int Ed 1999;38:3504-3506.
    • (1999) Angew Chem Int Ed , vol.38 , pp. 3504-3506
    • Yamada, K.1    Harwood, S.J.2    Groger, H.3    Shibasaki, M.4
  • 5
    • 1642369984 scopus 로고    scopus 로고
    • Chiral proton catalysis: A catalytic enantioselective direct aza-Henry reaction
    • Nugent BM, Yoder RA, Johnston JN. Chiral proton catalysis: A catalytic enantioselective direct aza-Henry reaction. J Am Chem Soc 2004;126:3418,3419.
    • (2004) J Am Chem Soc , vol.126 , pp. 3418
    • Nugent, B.M.1    Yoder, R.A.2    Johnston, J.N.3
  • 6
    • 0034807178 scopus 로고    scopus 로고
    • The first catalytic asymmetric aza-Henry reaction of nitronates with imines: A novel approach to optically active β-nitro-α-amino acid- and α,β-diamino acid derivatives
    • Knudsen KR, Risgaard T, Nishiwaki N, Gothelf KV, Jorgensen KA. The first catalytic asymmetric aza-Henry reaction of nitronates with imines: A novel approach to optically active β-nitro-α-amino acid- and α,β-diamino acid derivatives. J Am Chem Soc 2001;123:5843,5844.
    • (2001) J Am Chem Soc , vol.123 , pp. 5843
    • Knudsen, K.R.1    Risgaard, T.2    Nishiwaki, N.3    Gothelf, K.V.4    Jorgensen, K.A.5
  • 7
    • 0034143235 scopus 로고    scopus 로고
    • A new synthetic route to 1,3-oxazolidines via palladium-catalyzed regioselective [3+2] cycloaddition of vinylic oxiranes with imines
    • Shim JG, Yamamoto Y. A new synthetic route to 1,3-oxazolidines via palladium-catalyzed regioselective [3+2] cycloaddition of vinylic oxiranes with imines. Heterocycles 2000;52:885-895.
    • (2000) Heterocycles , vol.52 , pp. 885-895
    • Shim, J.G.1    Yamamoto, Y.2
  • 8
    • 0000510639 scopus 로고    scopus 로고
    • Ytterbium(III) Inflate/TMSCl: Efficient catalyst for imino ene reaction
    • Yamanaka M, Nishida A, Nakagawa M. Ytterbium(III) Inflate/TMSCl: Efficient catalyst for imino ene reaction. Org Lett 2000;2:159-161.
    • (2000) Org Lett , vol.2 , pp. 159-161
    • Yamanaka, M.1    Nishida, A.2    Nakagawa, M.3
  • 9
    • 0033601460 scopus 로고    scopus 로고
    • Rhodium-catalyzed arylation and alkenylation of imines with organostannanes
    • Oi S, Moro M, Fukuhara H, Kawanishi T, Inoue Y. Rhodium-catalyzed arylation and alkenylation of imines with organostannanes. Tetrahedron Lett 1999;40:9259-9262.
    • (1999) Tetrahedron Lett , vol.40 , pp. 9259-9262
    • Oi, S.1    Moro, M.2    Fukuhara, H.3    Kawanishi, T.4    Inoue, Y.5
  • 10
    • 0033617424 scopus 로고    scopus 로고
    • Aziridination of activated imines with monocarbonyl iodonium ylides generated from (Z)-(2-Acetoxyvinyl)iodonium salts via ester exchange: Stereoselective synthesis of 2-acylaziridines
    • Ochiai M, Kitagawa Y. Aziridination of activated imines with monocarbonyl iodonium ylides generated from (Z)-(2-Acetoxyvinyl)iodonium salts via ester exchange: Stereoselective synthesis of 2-acylaziridines. J Org Chem 1999;64:3181-3189.
    • (1999) J Org Chem , vol.64 , pp. 3181-3189
    • Ochiai, M.1    Kitagawa, Y.2
  • 11
    • 0000182934 scopus 로고    scopus 로고
    • A novel [3+2] cycloaddition approach to nitrogen heterocycles via phosphine-catalyzed reactions of 2,3-butadienoates or 2-butynoates and dimethyl acetylenedicarboxylate with imines: A convenient synthesis of pentabromopseudilin
    • Xu Z, Lu X. A novel [3+2] cycloaddition approach to nitrogen heterocycles via phosphine-catalyzed reactions of 2,3-butadienoates or 2-butynoates and dimethyl acetylenedicarboxylate with imines: A convenient synthesis of pentabromopseudilin. J Org Chem 1998;63:5031-5041.
    • (1998) J Org Chem , vol.63 , pp. 5031-5041
    • Xu, Z.1    Lu, X.2
  • 12
    • 0030919677 scopus 로고    scopus 로고
    • Phosphine-catalyzed [3+2] cycloaddition reaction of methyl 2,3-butadienoate and N-tosyl imines. A novel approach to nitrogen heterocycles
    • Xu Z, Lu X. Phosphine-catalyzed [3+2] cycloaddition reaction of methyl 2,3-butadienoate and N-tosyl imines. A novel approach to nitrogen heterocycles. Tetrahedron Lett 1997;38:3461-3464.
    • (1997) Tetrahedron Lett , vol.38 , pp. 3461-3464
    • Xu, Z.1    Lu, X.2
  • 13
    • 0001044209 scopus 로고    scopus 로고
    • A new reaction of imines with alkynyl sulfides affording α,β-unsaturated thioimidates
    • Ishitani H, Nagayama S, Kobayashi S. A new reaction of imines with alkynyl sulfides affording α,β-unsaturated thioimidates. J Org Chem 1996;61:1902,1903.
    • (1996) J Org Chem , vol.61 , pp. 1902
    • Ishitani, H.1    Nagayama, S.2    Kobayashi, S.3
  • 14
    • 0001324192 scopus 로고
    • 3-Substituted 2-acyl-1-sulfonylaziridines from the reaction of triphenylbismuthonium 2-oxoalkylides and N-sulfonylaldimines. Reversal of the cis/trans-isomer ratios depending on base and additive
    • Matano Y, Yoshimune M, Suzuki H. 3-Substituted 2-acyl-1- sulfonylaziridines from the reaction of triphenylbismuthonium 2-oxoalkylides and N-sulfonylaldimines. Reversal of the cis/trans-isomer ratios depending on base and additive. J Org Chem 1995;60:4663-4665.
    • (1995) J Org Chem , vol.60 , pp. 4663-4665
    • Matano, Y.1    Yoshimune, M.2    Suzuki, H.3
  • 15
    • 0000600584 scopus 로고
    • Inverse electron-demand Diels-Alder reactions of N-sulfonyl α,β-unsaturated imines: A general approach to implementation of the 4π participation of 1-aza-1,3-butadienes in Diels-Alder reactions
    • Boger DL, Corbett WL, Curran TT, Kasper AM. Inverse electron-demand Diels-Alder reactions of N-sulfonyl α,β-unsaturated imines: A general approach to implementation of the 4π participation of 1-aza-1,3-butadienes in Diels-Alder reactions. J Am Chem Soc 1991;113:1713-1729.
    • (1991) J Am Chem Soc , vol.113 , pp. 1713-1729
    • Boger, D.L.1    Corbett, W.L.2    Curran, T.T.3    Kasper, A.M.4
  • 16
    • 0001153217 scopus 로고
    • A convenient in situ procedure for effecting inter- and intramolecular Diels-Alder reactions of N-sulfonyl imines
    • Sisko J, Weinreb SM. A convenient in situ procedure for effecting inter- and intramolecular Diels-Alder reactions of N-sulfonyl imines. Tetrahedron Lett 1989;30:3037-3040.
    • (1989) Tetrahedron Lett , vol.30 , pp. 3037-3040
    • Sisko, J.1    Weinreb, S.M.2
  • 17
    • 0038106171 scopus 로고    scopus 로고
    • Additions of organometallic reagents to C:N bonds: Reactivity and selectivity
    • Bloch R. Additions of organometallic reagents to C:N bonds: Reactivity and selectivity. Chem Rev 1998;98:1407-1438.
    • (1998) Chem Rev , vol.98 , pp. 1407-1438
    • Bloch, R.1
  • 18
    • 0025912804 scopus 로고
    • The titanium tetrachloride induced synthesis of N-phosphinoylimines and N-sulfonylimines directly from aromatic aldehydes
    • Jennings WB, Lovely CJ. The titanium tetrachloride induced synthesis of N-phosphinoylimines and N-sulfonylimines directly from aromatic aldehydes. Tetrahedron 1991;47:5561-5568.
    • (1991) Tetrahedron , vol.47 , pp. 5561-5568
    • Jennings, W.B.1    Lovely, C.J.2
  • 19
    • 0033983411 scopus 로고    scopus 로고
    • An easy synthesis of aliphatic and aromatic N-sulfonyl aldimines
    • Chemla F, Hebbe V, Normant J. An easy synthesis of aliphatic and aromatic N-sulfonyl aldimines. Synthesis 2000:75-77.
    • (2000) Synthesis , pp. 75-77
    • Chemla, F.1    Hebbe, V.2    Normant, J.3
  • 20
    • 0343754067 scopus 로고
    • Heterocycles by diene synthesis. II. N-carbobutyloxymethylene-p- toluenesulfonamide, a new dienophile for the preparation of pyridine, piperideine, and piperidine derivatives by the Diels-Alder synthesis
    • Albrecht R, Kresze G. Heterocycles by diene synthesis. II. N-carbobutyloxymethylene-p-toluenesulfonamide, a new dienophile for the preparation of pyridine, piperideine, and piperidine derivatives by the Diels-Alder synthesis. Chem Ber 1965;98:1431.
    • (1965) Chem Ber , vol.98 , pp. 1431
    • Albrecht, R.1    Kresze, G.2
  • 22
    • 37049113129 scopus 로고
    • Removal of p-tolylsulfonyl groups from sulfonamides, Part 4. Synthesis of phenylglyyoxal imine monomers
    • McKay WR, Proctor GR. Removal of p-tolylsulfonyl groups from sulfonamides, Part 4. Synthesis of phenylglyyoxal imine monomers. J Chem Soc Perkin Trans 1 1981:2435-2442.
    • (1981) J Chem Soc Perkin Trans 1 , pp. 2435-2442
    • McKay, W.R.1    Proctor, G.R.2
  • 23
    • 0000574419 scopus 로고    scopus 로고
    • Solid-supported synthesis of imidazoles: A strategy for direct resin-attachment to the imidazole core
    • Bilodeau MT, Cunningham AM. Solid-supported synthesis of imidazoles: A strategy for direct resin-attachment to the imidazole core. J Org Chem 1998;63:2800,2801.
    • (1998) J Org Chem , vol.63 , pp. 2800
    • Bilodeau, M.T.1    Cunningham, A.M.2
  • 24
    • 0001494124 scopus 로고    scopus 로고
    • Imino Diels-Alder-based construction of a piperidine A-ring unit for total synthesis of the marine hepatotoxin cylindrospermopsin
    • Heintzelman GR, Weinreb SM, Parvez M. Imino Diels-Alder-based construction of a piperidine A-ring unit for total synthesis of the marine hepatotoxin cylindrospermopsin. J Org Chem 1996;61:4594-4599.
    • (1996) J Org Chem , vol.61 , pp. 4594-4599
    • Heintzelman, G.R.1    Weinreb, S.M.2    Parvez, M.3
  • 25
    • 0037415454 scopus 로고    scopus 로고
    • A practical synthesis of N-tosyl imines of aryl aldehydes
    • Lee KY, Lee CG, Kim JN. A practical synthesis of N-tosyl imines of aryl aldehydes. Tetrahedron Lett 2003;44:1231-1234.
    • (2003) Tetrahedron Lett , vol.44 , pp. 1231-1234
    • Lee, K.Y.1    Lee, C.G.2    Kim, J.N.3
  • 26
    • 0346150277 scopus 로고    scopus 로고
    • A new, mild synthesis of N-sulfonyl ketimines via the palladium-catalyzed isomerization of aziridines
    • Wolfe JP, Ney JE. A new, mild synthesis of N-sulfonyl ketimines via the palladium-catalyzed isomerization of aziridines. Org Lett 2003;5:4607-4610.
    • (2003) Org Lett , vol.5 , pp. 4607-4610
    • Wolfe, J.P.1    Ney, J.E.2
  • 27
    • 0035902842 scopus 로고    scopus 로고
    • Catalytic asymmetric direct Mannich reactions of carbonyl compounds with α-imino esters
    • Juhl K, Gathergood N, Jørgensen KA. Catalytic asymmetric direct Mannich reactions of carbonyl compounds with α-imino esters. Angew Chem Int Ed 2001;40:2995-2997.
    • (2001) Angew Chem Int Ed , vol.40 , pp. 2995-2997
    • Juhl, K.1    Gathergood, N.2    Jørgensen, K.A.3
  • 28
    • 0002829653 scopus 로고    scopus 로고
    • Mild, efficient cleavage of arene-sulfonamides by magnesium reduction
    • Nyasse B, Grehn L, Ragnarsson U. Mild, efficient cleavage of arene-sulfonamides by magnesium reduction. Chem Commun 1997:1017, 1018.
    • (1997) Chem Commun , pp. 1017
    • Nyasse, B.1    Grehn, L.2    Ragnarsson, U.3
  • 29
    • 0001209391 scopus 로고    scopus 로고
    • Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts
    • Ferraris D, Young B, Dudding T, Lectka T. Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts. J Am Chem Soc 1998;120:4548,4549.
    • (1998) J Am Chem Soc , vol.120 , pp. 4548
    • Ferraris, D.1    Young, B.2    Dudding, T.3    Lectka, T.4
  • 31
    • 0035833122 scopus 로고    scopus 로고
    • iPr)3, a highly efficient catalyst for the nitro-Mannich reaction
    • iPr)3, a highly efficient catalyst for the nitro-Mannich reaction. Tetrahedron Letter 2001;42:4673-4675.
    • (2001) Tetrahedron Letter , vol.42 , pp. 4673-4675
    • Qian, C.T.1    Gao, F.F.2    Chen, R.F.3
  • 32
    • 28444434073 scopus 로고    scopus 로고
    • The effect of coordination on the reaction of N-tosyl imines with diethylzinc
    • Gao FF, Deng MZ, Qian CT. The effect of coordination on the reaction of N-tosyl imines with diethylzinc. Tetrahedron 2005;61:12238-12243.
    • (2005) Tetrahedron , vol.61 , pp. 12238-12243
    • Gao, F.F.1    Deng, M.Z.2    Qian, C.T.3
  • 33
    • 0034614028 scopus 로고    scopus 로고
    • A direct catalytic enantioselective aldol reaction via a novel catalyst design
    • Trost BM, Ito H. A direct catalytic enantioselective aldol reaction via a novel catalyst design. J Am Chem Soc 2000;122:12003,12004.
    • (2000) J Am Chem Soc , vol.122 , pp. 12003
    • Trost, B.M.1    Ito, H.2
  • 34
    • 0036495323 scopus 로고    scopus 로고
    • A dinuclear Zn catalyst for the asymmetric nitro-aldol (Henry) reaction
    • Trost BM, Yeh VS. A dinuclear Zn catalyst for the asymmetric nitro-aldol (Henry) reaction. Angew Chem Int Ed 2002;41:861,862.
    • (2002) Angew Chem Int Ed , vol.41 , pp. 861
    • Trost, B.M.1    Yeh, V.S.2
  • 35
    • 0037438599 scopus 로고    scopus 로고
    • A direct catalytic asymmetric Mannich-type reaction to syn-amino alcohols
    • Trost BM, Terrell LR. A direct catalytic asymmetric Mannich-type reaction to syn-amino alcohols. J Am Chem Soc 2003;125:338,339.
    • (2003) J Am Chem Soc , vol.125 , pp. 338
    • Trost, B.M.1    Terrell, L.R.2
  • 36
    • 0345711474 scopus 로고    scopus 로고
    • Towards perfect asymmetric catalysis: Additives and cocatalysts
    • Vogl EM, Gröger VH, Shibasaki M. Towards perfect asymmetric catalysis: Additives and cocatalysts. Angew Chem Int Ed 1999;38:1570-1577.
    • (1999) Angew Chem Int Ed , vol.38 , pp. 1570-1577
    • Vogl, E.M.1    Gröger, V.H.2    Shibasaki, M.3


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