메뉴 건너뛰기




Volumn 46, Issue 20, 2007, Pages 3732-3734

Synthesis of highly functionalized chiral cyclopentanes by catalytic enantio- and diastereoselective double Michael addition reactions

Author keywords

Aldehydes; Cyclopentanes; Domino reactions; Michael addition; Organocatalysis

Indexed keywords

ADDITION REACTIONS; CATALYST ACTIVITY; ETHERS; STEREOSELECTIVITY;

EID: 34250849026     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700485     Document Type: Article
Times cited : (133)

References (59)
  • 1
    • 33847207721 scopus 로고    scopus 로고
    • For recent reviews of cascade reactions, see: a
    • For recent reviews of cascade reactions, see: a) K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292;
    • (2006) Angew. Chem , vol.118 , pp. 7292
    • Nicolaou, K.C.1    Edmonds, D.J.2    Bulger, P.G.3
  • 2
  • 4
  • 8
    • 11144263200 scopus 로고    scopus 로고
    • For recent reviews of organocatalysis, see: a
    • For recent reviews of organocatalysis, see: a) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
    • (2004) Angew. Chem , vol.116 , pp. 5248
    • Dalko, P.I.1    Moisan, L.2
  • 9
  • 10
    • 4143094833 scopus 로고    scopus 로고
    • Special issue on asymmetric organocatalysis: Acc. Chem. Res. 2004, 37, 487.
    • b) Special issue on asymmetric organocatalysis: Acc. Chem. Res. 2004, 37, 487.
  • 11
    • 34250678999 scopus 로고    scopus 로고
    • For a review of organocatalytic cascade reactions, see
    • For a review of organocatalytic cascade reactions, see: D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590;
    • (2007) Angew. Chem , vol.119 , pp. 1590
    • Enders, D.1    Grondal, C.2    Hüttl, M.R.M.3
  • 12
    • 33947198541 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 1570.
    • (2007) Chem. Int. Ed , vol.46 , pp. 1570
    • Angew1
  • 13
    • 34250661513 scopus 로고    scopus 로고
    • For selected examples of organocatalytic cascade reactions, see: a
    • For selected examples of organocatalytic cascade reactions, see: a) D. Enders, M. R. M. Hüttl, J. Runsink, G. Raabe, B. Wendt, Angew. Chem. 2007, 119, 471;
    • (2007) Angew. Chem , vol.119 , pp. 471
    • Enders, D.1    Hüttl, M.R.M.2    Runsink, J.3    Raabe, G.4    Wendt, B.5
  • 14
  • 16
    • 34248192461 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 1101;
    • (2007) Chem. Int. Ed , vol.46 , pp. 1101
    • Angew1
  • 25
  • 30
    • 33750307526 scopus 로고    scopus 로고
    • For Michael/aldol/dehydration reactions that have also been reported, see: a R. Rios, H. Sunden, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Córdova, Tetrahedron Lett. 2006, 47, 8547;
    • For Michael/aldol/dehydration reactions that have also been reported, see: a) R. Rios, H. Sunden, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Córdova, Tetrahedron Lett. 2006, 47, 8547;
  • 32
    • 0035136830 scopus 로고    scopus 로고
    • For reviews of double Michael addition reactions, see: a
    • For reviews of double Michael addition reactions, see: a) R. B. Grossman, Synlett 2001, 13;
    • (2001) Synlett , pp. 13
    • Grossman, R.B.1
  • 35
    • 33745191185 scopus 로고    scopus 로고
    • For selected examples of double Michael addition reactions, see: a
    • For selected examples of double Michael addition reactions, see: a) H. Yun, A. Gagnon, S. J. Danishefsky, Tetrahedron Lett. 2006, 47, 5311;
    • (2006) Tetrahedron Lett , vol.47 , pp. 5311
    • Yun, H.1    Gagnon, A.2    Danishefsky, S.J.3
  • 42
  • 45
    • 28944450864 scopus 로고    scopus 로고
    • Recently a thiourea was synthesized by using a hydrogen-bonding-mediated double Michael reaction, and although it is claimed to be a cascade process, the addition of a base (1,1,3,3-tetramethylguanidine or KOH) is essential for the second Michael reaction to occur; see: Y. Hoashi, T. Yabuta, P. Yuan, H. Miyabe, Y. Takemoto, Tetrahedron 2006, 62, 365.
    • Recently a thiourea was synthesized by using a hydrogen-bonding-mediated double Michael reaction, and although it is claimed to be a cascade process, the addition of a base (1,1,3,3-tetramethylguanidine or KOH) is essential for the second Michael reaction to occur; see: Y. Hoashi, T. Yabuta, P. Yuan, H. Miyabe, Y. Takemoto, Tetrahedron 2006, 62, 365.
  • 52
    • 34250669449 scopus 로고    scopus 로고
    • For a review of reactions catalyzed by chiral pyrrolinol ethers, see
    • For a review of reactions catalyzed by chiral pyrrolinol ethers, see: C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042;
    • (2006) Angew. Chem , vol.118 , pp. 8042
    • Palomo, C.1    Mielgo, A.2
  • 53
    • 33845505476 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7876.
    • (2006) Chem. Int. Ed , vol.45 , pp. 7876
    • Angew1
  • 54
    • 20444486476 scopus 로고    scopus 로고
    • For leading studies of reactions catalyzed by chiral pyrrolinol ethers, see: a
    • For leading studies of reactions catalyzed by chiral pyrrolinol ethers, see: a) M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804;
    • (2005) Angew. Chem , vol.117 , pp. 804
    • Marigo, M.1    Wabnitz, T.C.2    Fielenbach, D.3    Jørgensen, K.A.4
  • 55
  • 57
    • 22144459070 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4212;
    • (2005) Chem. Int. Ed , vol.44 , pp. 4212
    • Angew1
  • 59
    • 34250834146 scopus 로고    scopus 로고
    • The structure of the compound derived from 3j was determined by X-ray analysis. CCDC-635261 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
    • The structure of the compound derived from 3j was determined by X-ray analysis. CCDC-635261 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.