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Volumn 10, Issue , 2014, Pages 1536-1548

Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction

Author keywords

Asymmetric catalysis; Chiral phosphine ligands; Cyclopropane; Heck reaction; Organophosphorus; Transition metal catalysis

Indexed keywords


EID: 84904178090     PISSN: None     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.10.158     Document Type: Article
Times cited : (10)

References (72)
  • 3
    • 15044345663 scopus 로고    scopus 로고
    • Neighbouring-group effects in Heck reactions
    • DOI 10.1002/ejoc.200400711
    • Oestreich, M. Eur. J. Org. Chem. 2005, 783-792. doi:10.1002/ejoc. 200400711 (Pubitemid 40379879)
    • (2005) European Journal of Organic Chemistry , Issue.5 , pp. 783-792
    • Oestreich, M.1
  • 4
    • 2442562130 scopus 로고    scopus 로고
    • The development of the intramolecular asymmetric heck reaction
    • DOI 10.2174/1385272043370528
    • Guiry, P. J.; Kiely, D. Curr. Org. Chem. 2004, 8, 781-794. doi:10.2174/1385272043370528 (Pubitemid 38647482)
    • (2004) Current Organic Chemistry , vol.8 , Issue.9 , pp. 781-794
    • Guiry, P.J.1    Kiely, D.2
  • 6
    • 0042379984 scopus 로고    scopus 로고
    • doi:10.1021/cr020039h
    • Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945-2964. doi:10.1021/cr020039h
    • (2003) Chem. Rev , vol.103 , pp. 2945-2964
    • Dounay, A.B.1    Overman, L.E.2
  • 8
    • 34547166889 scopus 로고    scopus 로고
    • Total synthesis of complex cyclotryptamine alkaloids: Stereocontrolled construction of quaternary carbon stereocenters
    • DOI 10.1002/anie.200700612
    • Steven, A.; Overman, L. E. Angew. Chem., Int. Ed. 2007, 46, 5488-5508. doi:10.1002/anie.200700612 (Pubitemid 47121617)
    • (2007) Angewandte Chemie-International Edition , vol.46 , Issue.29 , pp. 5488-5508
    • Steven, A.1    Overman, L.E.2
  • 9
    • 84888261877 scopus 로고    scopus 로고
    • doi:10.1039/c3cc47551d
    • Liu, S.; Zhou, J. Chem. Commun. 2013, 49, 11758-11760. doi:10.1039/c3cc47551d
    • (2013) Chem. Commun , vol.49 , pp. 11758-11760
    • Liu, S.1    Zhou, J.2
  • 10
    • 84884506046 scopus 로고    scopus 로고
    • doi:10.1039/c3cc45233f
    • Hu, J.; Lu, Y.; Li, Y.; Zhou, J. Chem. Commun. 2013, 49, 9425-9427. doi:10.1039/c3cc45233f
    • (2013) Chem. Commun , vol.49 , pp. 9425-9427
    • Hu, J.1    Lu, Y.2    Li, Y.3    Zhou, J.4
  • 12
    • 84864271507 scopus 로고    scopus 로고
    • doi:10.1021/ja304099j
    • Yang, Z.; Zhou, J. J. Am. Chem. Soc. 2012, 134, 11833-11835. doi:10.1021/ja304099j
    • (2012) J. Am. Chem. Soc , vol.134 , pp. 11833-11835
    • Yang, Z.1    Zhou, J.2
  • 18
    • 0001562874 scopus 로고
    • doi:10.1016/0022-328X(92)83236-B
    • Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277. doi:10.1016/0022-328X(92)83236-B
    • (1992) J. Organomet. Chem , vol.428 , pp. 267-277
    • Ozawa, F.1    Hayashi, T.2
  • 19
    • 33751259639 scopus 로고    scopus 로고
    • Applications of 3,3-disubstituted BINAP derivatives in inter-and intramolecular Heck/Mizoroki reactions
    • DOI 10.1055/s-2006-950404
    • Hopkins, J. M.; Gorobets, E.; Wheatley, B. M. M.; Pravez, M.; Keay, B. A. Synlett 2006, 3120-3124. doi:10.1055/s-2006-950404 (Pubitemid 44800017)
    • (2006) Synlett , Issue.18 , pp. 3120-3124
    • Hopkins, J.M.1    Gorobets, E.2    Wheatley, B.M.M.3    Parvez, M.4    Keay, B.A.5
  • 20
    • 80053538385 scopus 로고    scopus 로고
    • doi:10.1002/chem.201101695
    • Wöste, T. H.; Oestreich, M. Chem.-Eur. J. 2011, 17, 11914-11918. doi:10.1002/chem.201101695
    • (2011) Chem.-Eur. J , vol.17 , pp. 11914-11918
    • Wöste, T.H.1    Oestreich, M.2
  • 21
    • 19044372134 scopus 로고    scopus 로고
    • Recent advances in biaryl-type bisphosphine ligands
    • DOI 10.1016/j.tet.2005.03.022, PII S0040402005004321
    • Shimizu, H.; Nagasaki, I.; Saito, T. Tetrahedron 2005, 61, 5405-5432. doi:10.1016/j.tet.2005.03.022 (Pubitemid 40712266)
    • (2005) Tetrahedron , vol.61 , Issue.23 , pp. 5405-5432
    • Shimizu, H.1    Nagasaki, I.2    Saito, T.3
  • 25
    • 33744470391 scopus 로고    scopus 로고
    • 2-BIPNOR: An easily accessible homologue of BIPNOR for asymmetric catalysis
    • DOI 10.1021/om060118+
    • Siutkowski, M.; Mercier, F.; Ricard, L.; Mathey, F. Organometallics 2006, 25, 2585-2589. doi:10.1021/om060118+ (Pubitemid 43798274)
    • (2006) Organometallics , vol.25 , Issue.10 , pp. 2585-2589
    • Siutkowski, M.1    Mercier, F.2    Ricard, L.3    Mathey, F.4
  • 26
    • 0038061495 scopus 로고    scopus 로고
    • A versatile route to planar chiral diphosphines and their application in the asymmetric Heck reaction
    • DOI 10.1016/S0957-4166(03)00204-0
    • Gibson, S. E.; Ibrahim, H.; Pasquier, C.; Swamy, V. M. Tetrahedron: Asymmetry 2003, 14, 1455-1458. doi:10.1016/S0957-4166(03)00204-0 (Pubitemid 36588842)
    • (2003) Tetrahedron Asymmetry , vol.14 , Issue.11 , pp. 1455-1458
    • Gibson, S.E.1    Ibrahim, H.2    Pasquier, C.3    Swamy, V.M.4
  • 27
    • 0742272121 scopus 로고    scopus 로고
    • Novel planar chiral diphosphines and their application in asymmetric hydrogenations and asymmetric Heck reactions
    • DOI 10.1016/j.tetasy.2003.11.014
    • Gibson, S. E.; Ibrahim, H.; Pasquier, C.; Swamy, V. M. Tetrahedron: Asymmetry 2004, 15, 465-473. doi:10.1016/j.tetasy.2003.11.014 (Pubitemid 38147673)
    • (2004) Tetrahedron Asymmetry , vol.15 , Issue.3 , pp. 465-473
    • Gibson, S.E.1    Ibrahim, H.2    Pasquier, C.3    Swamy, V.M.4
  • 30
  • 31
    • 0033815126 scopus 로고    scopus 로고
    • doi:10.1055/s-2000-7628
    • Tietze, L. F.; Thede, K. Synlett 2000, 1470-1472. doi:10.1055/s-2000-7628
    • (2000) Synlett , pp. 1470-1472
    • Tietze, L.F.1    Thede, K.2
  • 32
    • 1842737237 scopus 로고    scopus 로고
    • Synthesis, resolution and applications of 3,3-bis(RO)-MeO-BIPHEP derivatives
    • DOI 10.1016/j.tetlet.2004.03.073, PII S0040403904005866
    • Gorobets, E.; Sun, G.-R.; Wheatley, B. M. M.; Parvez, M.; Keay, B. A. Tetrahedron Lett. 2004, 45, 3597-3601. doi:10.1016/j.tetlet.2004.03.073 (Pubitemid 38481735)
    • (2004) Tetrahedron Letters , vol.45 , Issue.18 , pp. 3597-3601
    • Gorobets, E.1    Sun, G.-R.2    Wheatley, B.M.M.3    Parvez, M.4    Keay, B.A.5
  • 33
    • 0035910849 scopus 로고    scopus 로고
    • Synthesis, resolution and application of 2,2-bis(di-2-furylphosphino)-1, 1-binaphthalene
    • DOI 10.1016/S0957-4166(01)00035-0, PII S0957416601000350
    • Andersen, N. G.; McDonald, R.; Keay, B. A. Tetrahedron: Asymmetry 2001, 12, 263-269. doi:10.1016/S0957-4166(01)00035-0 (Pubitemid 32232200)
    • (2001) Tetrahedron Asymmetry , vol.12 , Issue.2 , pp. 263-269
    • Andersen, N.G.1    McDonald, R.2    Keay, B.A.3
  • 36
    • 36849024926 scopus 로고    scopus 로고
    • Chiral sulfur ligands for asymmetric catalysis
    • DOI 10.1021/cr068440h
    • Mellah, M.; Voituriez, A.; Schulz, E. Chem. Rev. 2007, 107, 5133-5209. doi:10.1021/cr068440h (Pubitemid 350225872)
    • (2007) Chemical Reviews , vol.107 , Issue.11 , pp. 5133-5209
    • Mellah, M.1    Voituriez, A.2    Schulz, E.3
  • 37
    • 0037380338 scopus 로고    scopus 로고
    • doi:10.1016/S1381-1169(02)00634-9
    • Kang, J.; Lee, J. H.; Im, K. S. J. Mol. Catal. A 2003, 196, 55-63. doi:10.1016/S1381-1169(02)00634-9
    • (2003) J. Mol. Catal. A , vol.196 , pp. 55-63
    • Kang, J.1    Lee, J.H.2    Im, K.S.3
  • 38
    • 1942501104 scopus 로고    scopus 로고
    • The first example of atropisomeric amide-derived P,O-ligands used for an asymmetric Heck reaction
    • DOI 10.1016/j.tet.2004.02.062, PII S0040402004003370
    • Dai, W.-M.; Yeung, K. K. Y.; Wang, Y. Tetrahedron 2004, 60, 4425-4430. doi:10.1016/j.tet.2004.02.062 (Pubitemid 38529906)
    • (2004) Tetrahedron , vol.60 , Issue.20 , pp. 4425-4430
    • Dai, W.-M.1    Yeung, K.K.Y.2    Wang, Y.3
  • 41
    • 0342647971 scopus 로고    scopus 로고
    • doi:10.1002/(SICI)1522-2675(19990908) 82:9〈1360::AID- HLCA1360〉3.3.CO;2-M
    • Kündig, E. P.; Meier, P. Helv. Chim. Acta 1999, 82, 1360-1370. doi:10.1002/(SICI)1522-2675(19990908)82:9〈1360::AID-HLCA1360〉3.3. CO;2-M
    • (1999) Helv. Chim. Acta , vol.82 , pp. 1360-1370
    • Kündig, E.P.1    Meier, P.2
  • 42
    • 0035897169 scopus 로고    scopus 로고
    • Modular pyridine-type P,N-ligands derived from monoterpenes: Application in asymmetric Heck addition
    • DOI 10.1016/S0040-4039(01)00369-0, PII S0040403901003690
    • Malkov, A. V.; Bella, M.; Stará, I. G.; Kočovský, P. Tetrahedron Lett. 2001, 42, 3045-3048. doi:10.1016/S0040-4039(01)00369-0 (Pubitemid 32276041)
    • (2001) Tetrahedron Letters , vol.42 , Issue.16 , pp. 3045-3048
    • Malkov, A.V.1    Bella, M.2    Stara, I.G.3    Kocovsky, P.4
  • 45
    • 0242269462 scopus 로고    scopus 로고
    • Chiral P,N-ligands with pyridine-nitrogen and phosphorus donor atoms. Syntheses and applications in asymmetric catalysis
    • DOI 10.1016/j.tet.2003.09.066
    • Chelucci, G.; Orrù, G.; Pinna, G. A. Tetrahedron 2003, 59, 9471-9515. doi:10.1016/j.tet.2003.09.066 (Pubitemid 37361080)
    • (2003) Tetrahedron , vol.59 , Issue.48 , pp. 9471-9515
    • Chelucci, G.1    Orru, G.2    Pinna, G.A.3
  • 46
    • 20444486960 scopus 로고    scopus 로고
    • A new class of readily available and conformationally rigid phosphino-oxazoline ligands for asymmetric catalysis
    • DOI 10.1016/j.tet.2005.03.111, PII S0040402005006150, Applications of Catalysis in Academia and Industry
    • Liu, D.; Dai, Q.; Zhang, X. Tetrahedron 2005, 61, 6460-6471. doi:10.1016/j.tet.2005.03.111 (Pubitemid 40812998)
    • (2005) Tetrahedron , vol.61 , Issue.26 , pp. 6460-6471
    • Liu, D.1    Dai, Q.2    Zhang, X.3
  • 47
    • 29444437987 scopus 로고    scopus 로고
    • Chiral phosphite-oxazolines: A new class of ligands for asymmetric Heck reactions
    • DOI 10.1021/ol052176h
    • Mata, Y.; Diéguez, M.; Pàmies, O.; Claver, C. Org. Lett. 2005, 7, 5597-5599. doi:10.1021/ol052176h (Pubitemid 43010808)
    • (2005) Organic Letters , vol.7 , Issue.25 , pp. 5597-5599
    • Mata, Y.1    Dieguez, M.2    Pamies, O.3    Claver, C.4
  • 51
    • 0034596065 scopus 로고    scopus 로고
    • An efficient phosphorus-containing oxazoline ligand derived from cis-2-amino-3,3-dimethyl-1-indanol: Application to the palladium-catalyzed asymmetric Heck reaction
    • DOI 10.1016/S0957-4166(00)00157-9, PII S0957416600001579
    • Hashimoto, Y.; Horie, Y.; Hayashi, M.; Saigo, K. Tetrahedron: Asymmetry 2000, 11, 2205-2210. doi:10.1016/S0957-4166(00)00157-9 (Pubitemid 30387020)
    • (2000) Tetrahedron Asymmetry , vol.11 , Issue.10 , pp. 2205-2210
    • Hashimoto, Y.1    Horie, Y.2    Hayashi, M.3    Saigo, K.4
  • 52
    • 0035798037 scopus 로고    scopus 로고
    • Proline-based P, N ligands in asymmetric allylation and the heck reaction
    • DOI 10.1021/jo0158231
    • Gilbertson, S. R.; Xie, D.; Fu, Z. J. Org. Chem. 2001, 66, 7240-7246. doi:10.1021/jo0158231 (Pubitemid 33029823)
    • (2001) Journal of Organic Chemistry , vol.66 , Issue.22 , pp. 7240-7246
    • Gilbertson, S.R.1    Xie, D.2    Fu, Z.3
  • 59
    • 0035945798 scopus 로고    scopus 로고
    • Chiral P,N-ligands based on ketopinic acid in the asymmetric heck reaction
    • DOI 10.1021/ol006747b
    • Gilbertson, S. R.; Fu, Z. Org. Lett. 2001, 3, 161-164. doi:10.1021/ol006747b (Pubitemid 33629356)
    • (2001) Organic Letters , vol.3 , Issue.2 , pp. 161-164
    • Gilbertson, S.R.1    Fu, Z.2
  • 60
    • 8644292512 scopus 로고    scopus 로고
    • Synthesis and application of chiral cyclopropane-based ligands in palladium-catalyzed allylic alkylation
    • DOI 10.1021/jo048782s
    • Molander, G. A.; Burke, J. P.; Carrol, P. J. J. Org. Chem. 2004, 69, 8062-8069. doi:10.1021/jo048782s (Pubitemid 39507418)
    • (2004) Journal of Organic Chemistry , vol.69 , Issue.23 , pp. 8062-8069
    • Molander, G.A.1    Burke, J.P.2    Carroll, P.J.3
  • 65
    • 0033605198 scopus 로고    scopus 로고
    • Enantiomerically pure 2,2-dibromocyclopropanecarboxylic acids, simple chiral building blocks
    • DOI 10.1016/S0040-4020(99)00048-4, PII S0040402099000484
    • Baird, M. S.; Licence, P.; Tverezovsky, V. V.; Bolesov, I. G.; Clegg, W. Tetrahedron 1999, 55, 2773-2784. doi:10.1016/S0040-4020(99)00048-4 (Pubitemid 29090531)
    • (1999) Tetrahedron , vol.55 , Issue.9 , pp. 2773-2784
    • Baird, M.S.1    Licence, P.2    Tverezovsky, V.V.3    Bolesov, I.G.4    Clegg, W.5
  • 66
    • 36749082898 scopus 로고    scopus 로고
    • Synthesis and structural characterization of enantiopure exo and endo six-membered oxazoline-derived palladacycles
    • DOI 10.1016/j.jorganchem.2007.10.011, PII S0022328X07007188
    • Mawo, R. Y.; Johnson, D. M.; Wood, J. L.; Smoliakova, I. P. J. Organomet. Chem. 2008, 693, 33-45. doi:10.1016/j.jorganchem.2007.10.011 (Pubitemid 350216109)
    • (2008) Journal of Organometallic Chemistry , vol.693 , Issue.1 , pp. 33-45
    • Mawo, R.Y.1    Johnson, D.M.2    Wood, J.L.3    Smoliakova, I.P.4
  • 67
    • 2942609239 scopus 로고    scopus 로고
    • Palladium complexes with ethylene-bridged bis(N-heterocyclic carbene) for C-C coupling reactions
    • DOI 10.1016/j.tet.2004.04.070, PII S0040402004006453
    • Lee, H. M.; Lu, C. Y.; Chen, C. Y.; Chen, W. L.; Lin, H. C.; Chiu, P. L.; Cheng, P. Y. Tetrahedron 2004, 60, 5807-5825. doi:10.1016/j.tet.2004.04.070 (Pubitemid 38757723)
    • (2004) Tetrahedron , vol.60 , Issue.27 , pp. 5807-5825
    • Lee, H.M.1    Lu, C.Y.2    Chen, C.Y.3    Chen, W.L.4    Lin, H.C.5    Chiu, P.L.6    Cheng, P.Y.7
  • 68
    • 0000030007 scopus 로고    scopus 로고
    • doi:10.1016/S0277-5387(99)00163-1
    • Benito, M.; López, C.; Morvan, X. Polyhedron 1999, 18, 2583-2595. doi:10.1016/S0277-5387(99)00163-1
    • (1999) Polyhedron , vol.18 , pp. 2583-2595
    • Benito, M.1    López, C.2    Morvan, X.3
  • 70
    • 0345120713 scopus 로고    scopus 로고
    • 2-symmetric bisphosphinobioxazoline as a chiral ligand. Highly enantioselective palladium-catalyzed allylic substitutions and formation of P,N,N,P tetradentate palladium (II) complexes
    • DOI 10.1021/jo990126i
    • Lee, S.; Lim, C. W.; Song, C. E.; Kim, K. M.; Jun, C. H. J. Org. Chem. 1999, 64, 4445-4451. doi:10.1021/jo990126i (Pubitemid 29293094)
    • (1999) Journal of Organic Chemistry , vol.64 , Issue.12 , pp. 4445-4451
    • Lee, S.-G.1    Lim, C.W.2    Song, C.E.3    Kim, K.M.4    Jun, C.H.5


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