메뉴 건너뛰기




Volumn 141, Issue 1, 2011, Pages 55-61

Practical one-pot synthesis of secondary amines by zinc-catalyzed reductive amination

Author keywords

Amination; Homogeneous catalysis; Hydrosilylation; Zinc

Indexed keywords

ALDEHYDES; AMINATION; CATALYSIS; CATALYSTS; HYDROSILYLATION; ZINC; ZINC COMPOUNDS;

EID: 79651472754     PISSN: 1011372X     EISSN: 1572879X     Source Type: Journal    
DOI: 10.1007/s10562-010-0463-4     Document Type: Article
Times cited : (63)

References (82)
  • 1
    • 0036736355 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD38XksFOrtLs%3D 10.1021/ar010065m
    • PT Anastas MM Kirchhoff 2002 Acc Chem Res 35 686 694 1:CAS:528: DC%2BD38XksFOrtLs%3D 10.1021/ar010065m
    • (2002) Acc Chem Res , vol.35 , pp. 686-694
    • Anastas, P.T.1    Kirchhoff, M.M.2
  • 2
    • 0035527722 scopus 로고    scopus 로고
    • Catalysis as a foundational pillar of green chemistry
    • DOI 10.1016/S0926-860X(01)00793-1, PII S0926860X01007931
    • PT Anastas MM Kirchhoff TC Williamson 2001 Appl Catal A 221 3 13 1:CAS:528:DC%2BD3MXptFCnsL8%3D 10.1016/S0926-860X(01)00793-1 (Pubitemid 34524097)
    • (2001) Applied Catalysis A: General , vol.221 , Issue.1-2 , pp. 3-13
    • Anastas, P.T.1    Kirchhoff, M.M.2    Williamson, T.C.3
  • 3
    • 77950154366 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BC3cXhs1yqsQ%3D%3D 10.1021/op9000548
    • JL Tucker 2010 Org Process Res Dev 14 328 331 1:CAS:528: DC%2BC3cXhs1yqsQ%3D%3D 10.1021/op9000548
    • (2010) Org Process Res Dev , vol.14 , pp. 328-331
    • Tucker, J.L.1
  • 4
    • 33645549833 scopus 로고    scopus 로고
    • Green chemistry, a pharmaceutical perspective
    • DOI 10.1021/op050227k
    • JL Tucker 2006 Org Process Res Dev 10 315 319 1:CAS:528: DC%2BD28XotlWrsA%3D%3D 10.1021/op050227k (Pubitemid 43508444)
    • (2006) Organic Process Research and Development , vol.10 , Issue.2 , pp. 315-319
    • Tucker, J.L.1
  • 9
    • 7044235263 scopus 로고    scopus 로고
    • 1:CAS:528:DyaK28XjsVOhsQ%3D%3D 10.1021/cr950027e
    • LF Tietze 1996 Chem Rev 96 115 136 1:CAS:528:DyaK28XjsVOhsQ%3D%3D 10.1021/cr950027e
    • (1996) Chem Rev , vol.96 , pp. 115-136
    • Tietze, L.F.1
  • 10
    • 70350511179 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1MXht12ht73P 10.1039/b816701j
    • A Padwa 2009 Chem Soc Rev 38 3072 3081 1:CAS:528:DC%2BD1MXht12ht73P 10.1039/b816701j
    • (2009) Chem Soc Rev , vol.38 , pp. 3072-3081
    • Padwa, A.1
  • 11
    • 70849124098 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1MXhsVahu7rJ 10.1002/chem.200901486
    • N Shindoh Y Takemoto K Takasu 2009 Chem Eur J 15 12168 12179 1:CAS:528:DC%2BD1MXhsVahu7rJ 10.1002/chem.200901486
    • (2009) Chem Eur J , vol.15 , pp. 12168-12179
    • Shindoh, N.1    Takemoto, Y.2    Takasu, K.3
  • 12
    • 34250021382 scopus 로고    scopus 로고
    • The domino way to heterocycles
    • DOI 10.1016/j.tet.2007.03.158, PII S0040402007006126
    • A Padwa SK Bur 2007 Tetrahedron 63 5341 5378 1:CAS:528: DC%2BD2sXlsFKhsrg%3D 10.1016/j.tet.2007.03.158 (Pubitemid 46881030)
    • (2007) Tetrahedron , vol.63 , Issue.25 , pp. 5341-5378
    • Padwa, A.1    Bur, S.K.2
  • 16
    • 85022146433 scopus 로고
    • 1:CAS:528:DyaK38Xot12hsw%3D%3D 10.1021/cr00009a001
    • DM Roundhill 1992 Chem Rev 92 1 27 1:CAS:528:DyaK38Xot12hsw%3D%3D 10.1021/cr00009a001
    • (1992) Chem Rev , vol.92 , pp. 1-27
    • Roundhill, D.M.1
  • 18
    • 0003445429 scopus 로고    scopus 로고
    • Jacobsen EN, Pfaltz A, Yamamoto H (eds) chap 6.3. Springer, New York
    • Nishiyama H (1999) In: Jacobsen EN, Pfaltz A, Yamamoto H (eds) Comprehensive asymmetric catalysis, chap 6.3. Springer, New York
    • (1999) Comprehensive Asymmetric Catalysis
    • Nishiyama, H.1
  • 20
    • 0034619216 scopus 로고    scopus 로고
    • Tararov VI, Kadyrov R, Riermeier TH, Börner A (2000) Chem Commun: 1867-1868
    • (2000) Chem Commun , pp. 1867-1868
    • Tararov Vi, K.1
  • 21
    • 0012975811 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD38Xjslyitrw%3D 10.1021/ol0200605
    • T Gross A Seayad A Moballigh M Beller 2002 Org Lett 4 2055 2058 1:CAS:528:DC%2BD38Xjslyitrw%3D 10.1021/ol0200605
    • (2002) Org Lett , vol.4 , pp. 2055-2058
    • Gross, T.1    Seayad, A.2    Moballigh, A.3    Beller, M.4
  • 25
    • 36849021012 scopus 로고    scopus 로고
    • One-pot reductive mono-N-alkylation of aniline and nitroarene derivatives using aldehydes
    • DOI 10.1021/jo701503q
    • E Byun B Hong KA De Castro M Lim H Rhee 2007 J Org Chem 72 9815 9817 1:CAS:528:DC%2BD2sXht12gsL3O 10.1021/jo701503q (Pubitemid 350231844)
    • (2007) Journal of Organic Chemistry , vol.72 , Issue.25 , pp. 9815-9817
    • Byun, E.1    Hong, B.2    De Castro, K.A.3    Lim, M.4    Rhee, H.5
  • 26
    • 70449629319 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1MXht12iurfL 10.1021/jo901787t
    • B Sreedhar PS Reddy DK Devi 2009 J Org Chem 74 8806 8809 1:CAS:528:DC%2BD1MXht12iurfL 10.1021/jo901787t
    • (2009) J Org Chem , vol.74 , pp. 8806-8809
    • Sreedhar, B.1    Reddy, P.S.2    Devi, D.K.3
  • 27
    • 56449127282 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1cXht1OlsLbI 10.1021/jo8016082
    • O-Y Lee K-L Law C-Y Ho D Yang 2008 J Org Chem 73 8829 8837 1:CAS:528:DC%2BD1cXht1OlsLbI 10.1021/jo8016082
    • (2008) J Org Chem , vol.73 , pp. 8829-8837
    • Lee, O.-Y.1    Law, K.-L.2    Ho, C.-Y.3    Yang, D.4
  • 28
    • 20444440795 scopus 로고    scopus 로고
    • Effective reductive amination of carbonyl compounds with hydrogen catalyzed by iridium complex in organic solvent and in ionic liquid
    • DOI 10.1016/j.tet.2005.05.024, PII S0040402005008021
    • D Imao S Fujihara T Yamamoto T Ohta Y Ito 2005 Tetrahedron 61 6988 6992 1:CAS:528:DC%2BD2MXltlenu7g%3D 10.1016/j.tet.2005.05.024 (Pubitemid 40814100)
    • (2005) Tetrahedron , vol.61 , Issue.29 , pp. 6988-6992
    • Imao, D.1    Fujihara, S.2    Yamamoto, T.3    Ohta, T.4    Ito, Y.5
  • 30
    • 0033582988 scopus 로고    scopus 로고
    • Reductive N-alkylation of amides, carbamates and ureas
    • DOI 10.1016/S0040-4039(99)00211-7, PII S0040403999002117
    • D Dubé AA Scholte 1999 Tetrahedron Lett 40 2295 2298 10.1016/S0040-4039(99)00211-7 (Pubitemid 29113132)
    • (1999) Tetrahedron Letters , vol.40 , Issue.12 , pp. 2295-2298
    • Dube, D.1    Scholte, A.A.2
  • 31
    • 0035847482 scopus 로고    scopus 로고
    • Novel triethylsilane mediated reductive N-alkylation of amines: Improved synthesis of 1-(4-imidazolyl)methyl-4-sulfonylbenzodiazepines, new farnesyltransferase inhibitors
    • DOI 10.1016/S0040-4039(00)02257-7, PII S0040403900022577
    • B-C Chen JE Sundeen P Guo MS Bednarz R Zhao 2001 Tetrahedron Lett 42 1245 1246 10.1016/S0040-4039(00)02257-7 (Pubitemid 32149783)
    • (2001) Tetrahedron Letters , vol.42 , Issue.7 , pp. 1245-1246
    • Chen, B.-C.1    Sundeen, J.E.2    Guo, P.3    Bednarz, M.S.4    Zhao, R.5
  • 32
    • 0000899213 scopus 로고    scopus 로고
    • Direct Reductive Amination of Aldehydes and Ketones Using Phenylsilane: Catalysis by Dibutyltin Dichloride
    • DOI 10.1021/ol015948s
    • R Apodaca W Xiao 2001 Org Lett 3 1745 1748 1:CAS:528:DC%2BD3MXjtFaksbk%3D 10.1021/ol015948s (Pubitemid 33631680)
    • (2001) Organic Letters , vol.3 , Issue.11 , pp. 1745-1748
    • Apodaca, R.1    Xiao, W.2
  • 33
    • 15444373515 scopus 로고    scopus 로고
    • Catalytic reductive alkylation of secondary amine with aldehyde and silane by an iridium compound
    • DOI 10.1021/jo0481708
    • T Mizuta S Sakaguchi Y Ishii 2005 J Org Chem 70 2195 2199 1:CAS:528:DC%2BD2MXht1ygt7k%3D 10.1021/jo0481708 (Pubitemid 40395157)
    • (2005) Journal of Organic Chemistry , vol.70 , Issue.6 , pp. 2195-2199
    • Mizuta, T.1    Sakaguchi, S.2    Ishii, Y.3
  • 34
    • 0000743790 scopus 로고    scopus 로고
    • 1:CAS:528:DyaK1cXhs1egug%3D%3D 10.1021/jo971117h
    • BC Ranu A Majee A Sarkar 1998 J Org Chem 63 370 373 1:CAS:528: DyaK1cXhs1egug%3D%3D 10.1021/jo971117h
    • (1998) J Org Chem , vol.63 , pp. 370-373
    • Ranu, B.C.1    Majee, A.2    Sarkar, A.3
  • 37
  • 39
    • 0033515563 scopus 로고    scopus 로고
    • Selective reduction of carbonyl compounds by polymethylhydrosiloxane in the presence of metal hydride catalysts
    • DOI 10.1021/jo982314z
    • H Mimoun 1999 J Org Chem 64 2582 2589 1:CAS:528:DyaK1MXhslyisLs%3D 10.1021/jo982314z (Pubitemid 29180495)
    • (1999) Journal of Organic Chemistry , vol.64 , Issue.7 , pp. 2582-2589
    • Mimoun, H.1
  • 40
    • 79957879909 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BC3cXovVCgtb0%3D 10.1002/cctc.201000036
    • NA Marinos S Enthaler M Driess 2010 ChemCatChem 2 846 853 1:CAS:528:DC%2BC3cXovVCgtb0%3D 10.1002/cctc.201000036
    • (2010) ChemCatChem , vol.2 , pp. 846-853
    • Marinos, N.A.1    Enthaler, S.2    Driess, M.3
  • 42
    • 77956028294 scopus 로고    scopus 로고
    • Enthaler S, Schröder K, Inoue S, Eckhardt B, Junge K, Beller M, Drie M (2010) Eur J Org Chem: 4893-4901
    • (2010) Eur J Org Chem , pp. 4893-4901
    • Enthaler S, S.1
  • 44
    • 1542375255 scopus 로고    scopus 로고
    • New developments in zinc-catalyzed asymmetric hydrosilylation of ketones with PMHS
    • DOI 10.1016/j.tet.2004.01.051, PII S0040402004001176
    • V Bette A Mortreux D Savoia J-F Carpentier 2004 Tetrahedron 60 2837 2842 1:CAS:528:DC%2BD2cXhslWltrs%3D 10.1016/j.tet.2004.01.051 (Pubitemid 38299306)
    • (2004) Tetrahedron , vol.60 , Issue.12 , pp. 2837-2842
    • Bette, V.1    Mortreux, A.2    Savoia, D.3    Carpentier, J.-F.4
  • 45
    • 0842310704 scopus 로고    scopus 로고
    • Use of diamines containing the -phenylethyl group as chiral ligands in the asymmetric hydrosilylation of prochiral ketones
    • DOI 10.1016/j.tet.2003.12.039
    • VM Mastranzo L Quinterno C Anaya de Parrodi E Juaristi PJ Walsh 2004 Tetrahedron 60 1781 1789 1:CAS:528:DC%2BD2cXpvFCntQ%3D%3D 10.1016/j.tet.2003.12. 039 (Pubitemid 38183068)
    • (2004) Tetrahedron , vol.60 , Issue.8 , pp. 1781-1789
    • Mastranzo, V.M.1    Quintero, L.2    De Parrodi, C.A.3    Juaristi, E.4    Walsh, P.J.5
  • 46
    • 15944425051 scopus 로고    scopus 로고
    • Asymmetric reduction of ortho-multisubstituted benzophenones catalyzed by diamine-Zn-diol complexes
    • DOI 10.1016/j.tetlet.2005.02.135
    • H Ushio K Mikami 2005 Tetrahedron Lett 46 2903 2906 1:CAS:528: DC%2BD2MXis1elu7g%3D 10.1016/j.tetlet.2005.02.135 (Pubitemid 40431765)
    • (2005) Tetrahedron Letters , vol.46 , Issue.16 , pp. 2903-2906
    • Ushio, H.1    Mikami, K.2
  • 47
    • 20444444374 scopus 로고    scopus 로고
    • Application of N,S-chelating chiral ligands and zinc complexes in catalytic asymmetric hydrosilylation using polymethylhydrosiloxane
    • DOI 10.1016/j.tetasy.2005.04.025, PII S0957416605003381
    • S Gérard Y Pressel O Riant 2005 Tetrahedron Asymmetr 16 1889 1891 10.1016/j.tetasy.2005.04.025 (Pubitemid 40812320)
    • (2005) Tetrahedron Asymmetry , vol.16 , Issue.11 , pp. 1889-1891
    • Gerard, S.1    Pressel, Y.2    Riant, O.3
  • 49
    • 66149141749 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1MXmvVahtLY%3D 10.1002/adsc.200800801
    • J Gajewy M Kwit J Gawroński 2009 Adv Synth Catal 351 1055 1063 1:CAS:528:DC%2BD1MXmvVahtLY%3D 10.1002/adsc.200800801
    • (2009) Adv Synth Catal , vol.351 , pp. 1055-1063
    • Gajewy, J.1    Kwit, M.2    Gawroński, J.3
  • 50
    • 77249133649 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BC3cXhtFagtbo%3D 10.1021/ja910083q
    • S Das D Addis K Junge M Beller 2010 J Am Chem Soc 132 1770 1771 1:CAS:528:DC%2BC3cXhtFagtbo%3D 10.1021/ja910083q
    • (2010) J Am Chem Soc , vol.132 , pp. 1770-1771
    • Das, S.1    Addis, D.2    Junge, K.3    Beller, M.4
  • 52
    • 15044358614 scopus 로고    scopus 로고
    • [Zinc-diamine]-catalyzed hydrosilylation of ketones in methanol. New developments and mechanistic insights
    • DOI 10.1002/adsc.200404283
    • V Bette A Mortreux D Savoia J-F Carpentier 2005 Adv Synth Catal 347 289 302 1:CAS:528:DC%2BD2MXit12nsrY%3D 10.1002/adsc.200404283 (Pubitemid 40380378)
    • (2005) Advanced Synthesis and Catalysis , vol.347 , Issue.2-3 , pp. 289-302
    • Bette, V.1    Mortreux, A.2    Savoia, D.3    Carpentier, J.-F.4
  • 54
    • 33745683612 scopus 로고    scopus 로고
    • Zinc-catalyzed enantioselective hydrosilylation of imines
    • DOI 10.1002/adsc.200606149
    • B-M Park S Mun J Yun 2006 Adv Synth Catal 348 1029 1032 1:CAS:528:DC%2BD28XmvV2lsL8%3D 10.1002/adsc.200606149 (Pubitemid 44000161)
    • (2006) Advanced Synthesis and Catalysis , vol.348 , Issue.9 , pp. 1029-1032
    • Park, B.-M.1    Mun, S.2    Yun, J.3
  • 55
    • 68149131336 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1MXotleitLY%3D 10.1021/ol901111g
    • O-Y Lee K-L Law D Yang 2009 Org Lett 11 3302 3305 1:CAS:528: DC%2BD1MXotleitLY%3D 10.1021/ol901111g
    • (2009) Org Lett , vol.11 , pp. 3302-3305
    • Lee, O.-Y.1    Law, K.-L.2    Yang, D.3
  • 59
    • 0037275463 scopus 로고    scopus 로고
    • N-methylpyrrolidine-zinc borohydride: As a new stable and efficient reducing agent in organic synthesis
    • DOI 10.1081/SCC-120015705
    • M Tajbakhsh MM Lakouraj F Mohanazadeh A Ahmadi-Nejhad 2003 Synth Commun 33 229 236 1:CAS:528:DC%2BD3sXhtlCnsrY%3D 10.1081/SCC-120015705 (Pubitemid 36194124)
    • (2003) Synthetic Communications , vol.33 , Issue.2 , pp. 229-236
    • Tajbakhsh, M.1    Lakouraj, M.M.2    Mohanazadeh, F.3    Ahmadi-Nejhad, A.4
  • 66
    • 0001767754 scopus 로고
    • 1:CAS:528:DyaE3cXhtFWmu7g%3D 10.1021/ja00710a028
    • GJ Kubas DF Shriver 1970 J Am Chem Soc 92 1949 1954 1:CAS:528: DyaE3cXhtFWmu7g%3D 10.1021/ja00710a028
    • (1970) J Am Chem Soc , vol.92 , pp. 1949-1954
    • Kubas, G.J.1    Shriver, D.F.2
  • 68
    • 0030837316 scopus 로고    scopus 로고
    • 1:CAS:528:DyaK2sXhs1CrsrY%3D 10.1021/jp9617332
    • Y Wang RA Poirier 1997 J Phys Chem A 101 907 912 1:CAS:528: DyaK2sXhs1CrsrY%3D 10.1021/jp9617332
    • (1997) J Phys Chem A , vol.101 , pp. 907-912
    • Wang, Y.1    Poirier, R.A.2
  • 71
    • 67449083081 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1MXlsFCks7s%3D 10.1039/b901929d
    • R Martinez DJ Ramon M Yus 2009 Org Biomol Chem 7 2176 2181 1:CAS:528:DC%2BD1MXlsFCks7s%3D 10.1039/b901929d
    • (2009) Org Biomol Chem , vol.7 , pp. 2176-2181
    • Martinez, R.1    Ramon, D.J.2    Yus, M.3
  • 72
    • 0035128037 scopus 로고    scopus 로고
    • Mechanism of insertion of carbodiimides into the Zr-C bonds of zirconaaziridines. Formation of -amino amidines
    • DOI 10.1021/om000768s
    • JA Tunge CJ Czerwinski DA Gately JR Norton 2001 Organometallics 20 254 260 1:CAS:528:DC%2BD3cXos1ajtrc%3D 10.1021/om000768s (Pubitemid 32134524)
    • (2001) Organometallics , vol.20 , Issue.2 , pp. 254-260
    • Tunge, J.A.1    Czerwinski, C.J.2    Gately, D.A.3    Norton, J.R.4
  • 74
    • 8644224810 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD2cXpsVGqsrY%3D 10.1016/j.poly.2004.07.001
    • JR Miecznikowski RH Crabtree 2004 Polyhedron 23 2857 2872 1:CAS:528:DC%2BD2cXpsVGqsrY%3D 10.1016/j.poly.2004.07.001
    • (2004) Polyhedron , vol.23 , pp. 2857-2872
    • Miecznikowski, J.R.1    Crabtree, R.H.2
  • 75
    • 0001436503 scopus 로고
    • 1:CAS:528:DyaL3sXktFylurg%3D 10.1016/S0040-4020(01)91910-6
    • JB Steevens UK Pandit 1983 Tetrahedron 39 1395 1400 1:CAS:528: DyaL3sXktFylurg%3D 10.1016/S0040-4020(01)91910-6
    • (1983) Tetrahedron , vol.39 , pp. 1395-1400
    • Steevens, J.B.1    Pandit, U.K.2
  • 78
    • 38349149292 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1cXlt1WisLo%3D 10.1002/adsc.200700344
    • R He PH Toy Y Lam 2008 Adv Synth Catal 350 54 60 1:CAS:528: DC%2BD1cXlt1WisLo%3D 10.1002/adsc.200700344
    • (2008) Adv Synth Catal , vol.350 , pp. 54-60
    • He, R.1    Toy, P.H.2    Lam, Y.3
  • 79
    • 37649000780 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD1cXlt1ajtQ%3D%3D 10.1016/j.tet.2007.11.074
    • RE Meadows S Woodward 2008 Tetrahedron 64 1218 1224 1:CAS:528: DC%2BD1cXlt1ajtQ%3D%3D 10.1016/j.tet.2007.11.074
    • (2008) Tetrahedron , vol.64 , pp. 1218-1224
    • Meadows, R.E.1    Woodward, S.2
  • 81
    • 4143066159 scopus 로고    scopus 로고
    • A selective reductive amination of aldehydes by the use of Hantzsch dihydropyridines as reductant
    • DOI 10.1016/j.tet.2004.05.096, PII S0040402004008427
    • T Itoh K Nagata M Miyazaki H Ishikawa A Kurihara A Ohsawa 2004 Tetrahedron 60 6649 6655 1:CAS:528:DC%2BD2cXmtFKkt7w%3D 10.1016/j.tet.2004.05. 096 (Pubitemid 39090263)
    • (2004) Tetrahedron , vol.60 , Issue.31 , pp. 6649-6655
    • Itoh, T.1    Nagata, K.2    Miyazaki, M.3    Ishikawa, H.4    Kurihara, A.5    Ohsawa, A.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.