메뉴 건너뛰기




Volumn 352, Issue 17, 2010, Pages 2863-2868

Asymmetric synthesis of polyfunctionalized pyrrolidines via a thiourea catalyzed domino Mannich/aza-Michael reaction

Author keywords

bifunctional thioureas; domino reaction; Mannich aza Michael reaction; organocatalysis; pyrrolidines

Indexed keywords


EID: 78649614746     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000658     Document Type: Article
Times cited : (42)

References (117)
  • 6
    • 48849094479 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 4638-4660
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4638-4660
  • 11
    • 53549121402 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 6138-6171
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6138-6171
  • 14
    • 70350506798 scopus 로고    scopus 로고
    • for special issues on organocatalysis, see
    • D. Enders, C. Wang, J. X. Liebich, Chem. Eur. J. 2009, 15, 11058-11076; for special issues on organocatalysis, see
    • (2009) Chem. Eur. J. , vol.15 , pp. 11058-11076
    • Enders, D.1    Wang, C.2    Liebich, J.X.3
  • 18
    • 38349142750 scopus 로고    scopus 로고
    • B. List, (guest editor), Chem. Rev. 2007, 107, 5413-5415.
    • (2007) Chem. Rev. , vol.107 , pp. 5413-5415
    • List, B.1
  • 20
    • 33947198541 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 1570-1581
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 1570-1581
  • 33
    • 23744473863 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4877-4880
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4877-4880
  • 35
    • 33845329553 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7832-7835.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 7832-7835
  • 48
    • 78649576192 scopus 로고    scopus 로고
    • For selected examples, see
    • For selected examples, see
  • 52
  • 54
  • 55
    • 0034750244 scopus 로고    scopus 로고
    • B. List, Synlett 2001, 1675-1686
    • (2001) Synlett , pp. 1675-1686
    • List, B.1
  • 56
    • 0037043180 scopus 로고    scopus 로고
    • B. List, Tetrahedron 2002, 58, 5573-5590
    • (2002) Tetrahedron , vol.58 , pp. 5573-5590
    • List, B.1
  • 63
    • 26844568111 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 6272-6276
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 6272-6276
  • 66
    • 33947231700 scopus 로고    scopus 로고
    • For selected organocatalytic examples, see
    • H. Pellissier, Tetrahedron 2007, 63, 3235-3285. For selected organocatalytic examples, see
    • (2007) Tetrahedron , vol.63 , pp. 3235-3285
    • Pellissier, H.1
  • 87
    • 70349995077 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 7604-7607
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7604-7607
  • 90
    • 33847620405 scopus 로고    scopus 로고
    • for a recent review on the N-acylimine chemistry, see
    • for a recent review on the N-acylimine chemistry, see:, M. Petrini, E. Torregiani, Synthesis 2007, 159-186.
    • (2007) Synthesis , pp. 159-186
    • Petrini, M.1    Torregiani, E.2
  • 97
    • 54749100733 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 7539-7542
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7539-7542
  • 106
    • 34250849026 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 3732-3734.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 3732-3734
  • 107
    • 78649568868 scopus 로고    scopus 로고
    • For the synthesis of malonate-α,β-unsaturated esters 2a-c we used a modified procedure from
    • For the synthesis of malonate-α,β-unsaturated esters 2a-c we used a modified procedure from
  • 108
    • 85026872712 scopus 로고    scopus 로고
    • For the synthesis of malonate-α,β-unsaturated ester 2d we used a modified procedure from
    • A. Padwa, S. H. Watterson, Z. Ni, Org. Synth. 1997, 74, 147. For the synthesis of malonate-α,β-unsaturated ester 2d we used a modified procedure from
    • (1997) Org. Synth. , vol.74 , pp. 147
    • Padwa, A.1    Watterson, S.H.2    Ni, Z.3
  • 109
    • 0001563584 scopus 로고
    • Experimental details are provided in the Supporting Information
    • B. M. Trost, C.-J. Li, J. Am. Chem. Soc. 1994, 116, 3167-3168. Experimental details are provided in the Supporting Information.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 3167-3168
    • Trost, B.M.1    Li, C.-J.2
  • 113
    • 33644747543 scopus 로고    scopus 로고
    • Unfortunately, aliphatic alidimines did not give satisfactory results with our protocol
    • A. L. Tillmann, J. Ye, D. J. Dixon, Chem. Commun. 2006, 1191-1193. Unfortunately, aliphatic alidimines did not give satisfactory results with our protocol.
    • (2006) Chem. Commun. , pp. 1191-1193
    • Tillmann, A.L.1    Ye, J.2    Dixon, D.J.3
  • 114
    • 0142072631 scopus 로고    scopus 로고
    • For the synthesis of thiourea catalysts 4, see: (4a) (4b)
    • For the synthesis of thiourea catalysts 4, see: (4a), T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672-12673; (4b)
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12672-12673
    • Okino, T.1    Hoashi, Y.2    Takemoto, Y.3
  • 116
    • 78649628318 scopus 로고    scopus 로고
    • Crystallographic data for rac -8a and (R,R)- 8d reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 789982 (rac- 8a) and CCDC 790099 (8d). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via or on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax.: (internat.) +44-1223/336-033; e-mail: deposit@ ccdc.cam.ac.uk]
    • Crystallographic data for rac -8a and (R,R)- 8d reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 789982 (rac- 8a) and CCDC 790099 (8d). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via or on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax.: (internat.) +44-1223/336-033; e-mail: deposit@ ccdc.cam.ac.uk].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.