메뉴 건너뛰기




Volumn 7, Issue , 2011, Pages 781-785

Highly efficient gold(I)-catalyzed Overman rearrangement in water

Author keywords

Allylic trichloroacetamides; Allylic trichloroacetimidate; Gold(I) chloride; Overman rearrangement; Water

Indexed keywords


EID: 79958824132     PISSN: 18605397     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.7.88     Document Type: Article
Times cited : (9)

References (37)
  • 1
    • 0000832159 scopus 로고
    • doi:10.1021/ja00809a054
    • Overman, L. E. J. Am. Chem. Soc. 1974, 96, 597-599. doi:10.1021/ ja00809a054
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 597-599
    • Overman, L.E.1
  • 2
    • 33847798567 scopus 로고
    • doi:10.1021/ja00426a038
    • Overman, L. E. J. Am. Chem. Soc. 1976, 98, 2901-2910. doi:10.1021/ja00426a038
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 2901-2910
    • Overman, L.E.1
  • 3
    • 0001741549 scopus 로고
    • doi:10.1021/ar50151a005
    • Overman, L. E. Acc. Chem. Res. 1980, 13, 218-224. doi:10.1021/ar50151a005
    • (1980) Acc. Chem. Res. , vol.13 , pp. 218-224
    • Overman, L.E.1
  • 5
    • 0026515878 scopus 로고
    • doi:10.1016/S0040-4020(01)88203-X
    • Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071-1080. doi:10.1016/S0040-4020(01)88203-X
    • (1992) Tetrahedron , vol.48 , pp. 1071-1080
    • Metz, P.1    Mues, C.2    Schoop, A.3
  • 7
    • 43449096064 scopus 로고    scopus 로고
    • Overman, L. E., Ed.; Wiley: Hoboken, NJ
    • Overman, L. E.; Carpenter, N. E. In Organic Reactions; Overman, L. E., Ed.; Wiley: Hoboken, NJ, 2005; Vol. 66, pp 653-760.
    • (2005) Organic Reactions , vol.66 , pp. 653-760
    • Overman, L.E.1    Carpenter, N.E.2
  • 8
    • 77955182952 scopus 로고    scopus 로고
    • doi:10.1002/asia.201000131
    • Nomura, H.; Richards, C. J. Chem.-Asian J. 2010, 5, 1726-1740. doi:10.1002/asia.201000131
    • (2010) Chem.-Asian J. , vol.5 , pp. 1726-1740
    • Nomura, H.1    Richards, C.J.2
  • 9
    • 0008248125 scopus 로고    scopus 로고
    • doi:10.1016/S0022-328X(98)01065-1
    • Hollis, T. K.; Overman, L. E. J. Organomet. Chem. 1999, 576, 290-299. doi:10.1016/S0022-328X(98)01065-1
    • (1999) J. Organomet. Chem. , vol.576 , pp. 290-299
    • Hollis, T.K.1    Overman, L.E.2
  • 10
    • 0141885409 scopus 로고    scopus 로고
    • Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity
    • DOI 10.1021/ja037086r
    • Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412-12413. doi:10.1021/ja037086r (Pubitemid 37254751)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.41 , pp. 12412-12413
    • Anderson, C.E.1    Overman, L.E.2
  • 11
    • 8644276255 scopus 로고    scopus 로고
    • Monomeric Cobalt Oxazoline Palladacycles (COP). Useful catalysts for catalytic asymmetric rearrangement of allylic trichloroacetimidates
    • DOI 10.1021/jo0487092
    • Kirsch, S. F.; Overman, L. E.; Watson, M. P. J. Org. Chem. 2004, 69, 8101-8104. doi:10.1021/jo0487092 (Pubitemid 39507422)
    • (2004) Journal of Organic Chemistry , vol.69 , Issue.23 , pp. 8101-8104
    • Kirsch, S.F.1    Overman, L.E.2    Watson, M.P.3
  • 12
    • 34247531301 scopus 로고    scopus 로고
    • Kinetic and computational analysis of the palladium(II)-catalyzed asymmetric allylic trichloroacetimidate rearrangement: Development of a model for enantioselectivity
    • DOI 10.1021/ja0676962
    • Watson, M. P.; Overman, L. E.; Bergman, R. G. J. Am. Chem. Soc. 2007, 129, 5031-5044. doi:10.1021/ja0676962 (Pubitemid 46651382)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.16 , pp. 5031-5044
    • Watson, M.P.1    Overman, L.E.2    Bergman, R.G.3
  • 14
    • 33845471185 scopus 로고
    • doi:10.1021/cr00061a001
    • Lutz, R. P. Chem. Rev. 1984, 84, 205-247. doi:10.1021/cr00061a001
    • (1984) Chem. Rev. , vol.84 , pp. 205-247
    • Lutz, R.P.1
  • 15
    • 36949037942 scopus 로고    scopus 로고
    • Catalysis of the Claisen rearrangement
    • DOI 10.1016/j.tet.2007.10.079, PII S0040402007018157
    • Majumdar, K. C.; Alam, S.; Chattopadhyay, B. Tetrahedron 2008, 64, 597-643. doi:10.1016/j.tet.2007.10.079 (Pubitemid 350237684)
    • (2008) Tetrahedron , vol.64 , Issue.4 , pp. 597-643
    • Majumdar, K.C.1    Alam, S.2    Chattopadhyay, B.3
  • 16
    • 34249006882 scopus 로고    scopus 로고
    • Propargylic esters in gold catalysis: Access to diversity
    • DOI 10.1002/anie.200604773
    • Marion, N.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750-2752. doi:10.1002/anie.200604773 (Pubitemid 46981270)
    • (2007) Angewandte Chemie - International Edition , vol.46 , Issue.16 , pp. 2750-2752
    • Marion, N.1    Nolan, S.P.2
  • 17
    • 28844458694 scopus 로고    scopus 로고
    • Tandem Au-catalyzed 3,3-rearrangement-[2 + 2] cycloadditions of propargylic esters: Expeditious access to highly functionalized 2,3-indoline-fused cyclobutanes
    • DOI 10.1021/ja056419c
    • Zhang, L. J. Am. Chem. Soc. 2005, 127, 16804-16805. doi:10.1021/ja056419c (Pubitemid 41772838)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.48 , pp. 16804-16805
    • Zhang, L.1
  • 19
    • 33646459632 scopus 로고    scopus 로고
    • Gold(I)-catalyzed stereoselective formation of functionalized 2,5-dihydrofurans
    • DOI 10.1021/ol0606839
    • Buzas, A.; Istrate, F.; Gagosz, F. Org. Lett. 2006, 8, 1957-1959. doi:10.1021/ol0606839 (Pubitemid 43692199)
    • (2006) Organic Letters , vol.8 , Issue.9 , pp. 1957-1959
    • Buzas, A.1    Istrate, F.2    Gagosz, F.3
  • 20
    • 32244445098 scopus 로고    scopus 로고
    • Efficient synthesis of cyclopentenones from enynyl acetates via tandem Au(I)-catalyzed 3,3-rearrangement and the Nazarov reaction
    • DOI 10.1021/ja057327q
    • Zhang, L.; Wang, S. J. Am. Chem. Soc. 2006, 128, 1442-1443. doi:10.1021/ja057327q (Pubitemid 43214844)
    • (2006) Journal of the American Chemical Society , vol.128 , Issue.5 , pp. 1442-1443
    • Zhang, L.1    Wang, S.2
  • 21
    • 33745700263 scopus 로고    scopus 로고
    • doi:10.1021/ja062777j
    • Wang, S.; Zhang, L. J. Am. Chem. Soc. 2006, 128, 8414-8415. doi:10.1021/ja062777j
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 8414-8415
    • Wang, S.1    Zhang, L.2
  • 25
    • 28844460443 scopus 로고    scopus 로고
    • Novel catalysts for the overman rearrangement
    • DOI 10.1055/s-2005-918952, D24105ST
    • Jaunzeme, I.; Jirgensons, A. Synlett 2005, 2984-2986. doi:10.1055/s-2005-918952 (Pubitemid 41779617)
    • (2005) Synlett , Issue.19 , pp. 2984-2986
    • Jaunzeme, I.1    Jirgensons, A.2
  • 26
    • 33746254995 scopus 로고    scopus 로고
    • Scope and limitations of ether-directed, metal-catalysed aza-Claisen rearrangements; Improved stereoselectivity using non-coordinating solvents
    • DOI 10.1039/b607014k
    • Jamieson, A. G.; Sutherland, A. Org. Biomol. Chem. 2006, 4, 2932-2937. doi:10.1039/b607014k (Pubitemid 44100293)
    • (2006) Organic and Biomolecular Chemistry , vol.4 , Issue.15 , pp. 2932-2937
    • Jamieson, A.G.1    Sutherland, A.2
  • 27
    • 34247576692 scopus 로고    scopus 로고
    • A stereoselective synthesis of (2R,3S)-2-amino-3,4-dihydroxybutyric acid using an ether directed aza-Claisen rearrangement
    • DOI 10.1016/j.tetlet.2007.03.161, PII S0040403907006375
    • Swift, M. D.; Sutherland, A. Tetrahedron Lett. 2007, 48, 3771-3773. doi:10.1016/j.tetlet.2007.03.161 (Pubitemid 46669667)
    • (2007) Tetrahedron Letters , vol.48 , Issue.22 , pp. 3771-3773
    • Swift, M.D.1    Sutherland, A.2
  • 28
    • 43449139968 scopus 로고    scopus 로고
    • doi:10.1016/j.tet.2008.03.099
    • Jaunzeme, I.; Jirgensons, A. Tetrahedron 2008, 64, 5794-5799. doi:10.1016/j.tet.2008.03.099
    • (2008) Tetrahedron , vol.64 , pp. 5794-5799
    • Jaunzeme, I.1    Jirgensons, A.2
  • 29
    • 77749273784 scopus 로고    scopus 로고
    • doi:10.1021/ol100056f
    • Xing, D.; Yang, D. Org. Lett. 2010, 12, 1068-1071. doi:10.1021/ol100056f
    • (2010) Org. Lett. , vol.12 , pp. 1068-1071
    • Xing, D.1    Yang, D.2
  • 30
    • 34247874745 scopus 로고    scopus 로고
    • A golden future for green chemistry
    • DOI 10.1016/j.cattod.2007.01.018, PII S0920586107000296, Gold 2006: New Industrial Applications for Gold - Selected papers on catalysis from the 4th International Conference on Gold Science, Technology and its Applications, University of Limerick
    • Hutchings, G. J. Catal. Today 2007, 122, 196-200. doi:10.1016/j.cattod. 2007.01.018 (Pubitemid 46702504)
    • (2007) Catalysis Today , vol.122 , Issue.3-4 , pp. 196-200
    • Hutchings, G.J.1
  • 31
    • 0042125406 scopus 로고    scopus 로고
    • A highly efficient three-component coupling of aldehyde, alkyne, and amines via C-H activation catalyzed by gold in water
    • DOI 10.1021/ja0359299
    • Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584-9585. doi:10.1021/ja0359299 (Pubitemid 36975910)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.32 , pp. 9584-9585
    • Wei, C.1    Li, C.-J.2
  • 32
    • 33748272697 scopus 로고    scopus 로고
    • Diastereoselective synthesis of oxyamines via gold-, silver- and copper-catalyzed, three-component couplings of oxyaldehydes, alkynes, and amines in water
    • DOI 10.1002/adsc.200606118
    • Huang, B.; Yao, X.; Li, C.-J. Adv. Synth. Catal. 2006, 348, 1528-1532. doi:10.1002/adsc.200606118 (Pubitemid 44318748)
    • (2006) Advanced Synthesis and Catalysis , vol.348 , Issue.12-13 , pp. 1528-1532
    • Huang, B.1    Yao, X.2    Li, C.-J.3
  • 33
    • 33646439990 scopus 로고    scopus 로고
    • Gold(III) salen complex-catalyzed synthesis of propargylamines via a three-component coupling reaction
    • DOI 10.1021/ol0528641
    • Lo, V. K.-Y.; Liu, Y.; Wong, M.-K.; Che, C.-M. Org. Lett. 2006, 8, 1529-1532. doi:10.1021/ol0528641 (Pubitemid 43691076)
    • (2006) Organic Letters , vol.8 , Issue.8 , pp. 1529-1532
    • Lo, V.K.-Y.1    Liu, Y.2    Wong, M.-K.3    Che, C.-M.4
  • 34
    • 33644784644 scopus 로고    scopus 로고
    • Gold(I)-catalyzed oxidative cleavage of a C-C double bond in water
    • DOI 10.1021/ol052830t
    • Xing, D.; Guan, B.; Cai, G.; Fang, Z.; Yang, L.; Shi, Z. Org. Lett. 2006, 8, 693-696. doi:10.1021/ol052830t (Pubitemid 43341992)
    • (2006) Organic Letters , vol.8 , Issue.4 , pp. 693-696
    • Xing, D.1    Guan, B.2    Cai, G.3    Fang, Z.4    Yang, L.5    Shi, Z.6
  • 37
    • 0028298630 scopus 로고
    • Vigabatrin synthesis by thermal rearrangements
    • DOI 10.1016/S0040-4039(00)76824-9
    • Casara, P. Tetrahedron Lett. 1994, 35, 3049-3050. doi:10.1016/S0040- 4039(00)76824-9 (Pubitemid 24162669)
    • (1994) Tetrahedron Letters , vol.35 , Issue.19 , pp. 3049-3050
    • Casara, P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.