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Volumn 14, Issue 16, 2008, Pages 4788-4791

Quaternary stereogenic carbon atoms in complex molecules by an asymmetric, organocatalytic, triple-cascade reaction

Author keywords

Asymmetric synthesis; Domino reactions; Multicomponent reactions; Organocatalysis; Quaternary stereocenters

Indexed keywords

AMINES; ATOMIC PHYSICS; CARBON; CARBONYLATION; CATALYSIS; COMPLEXATION; OLEFINS; ORGANIC COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 46149106243     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800440     Document Type: Article
Times cited : (103)

References (52)
  • 7
    • 33750977591 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7134-7186;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 7134-7186
  • 10
    • 17144366282 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 1602-1634.
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 1602-1634
  • 11
    • 34547204175 scopus 로고    scopus 로고
    • Ed, Rl. Dalko, Wiley-VCH, Weinheim
    • General reviews on asymmetric organocatalysis, see: a) Enantioselective Organocatalysis (Ed.: Rl. Dalko), Wiley-VCH, Weinheim, 2007;
    • (2007) Enantioselective Organocatalysis
  • 14
    • 34250678999 scopus 로고    scopus 로고
    • Reviews on organocatalytic domino reactions: a
    • Reviews on organocatalytic domino reactions: a) D. Enders, C. Grondai, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590-1601;
    • (2007) Angew. Chem , vol.119 , pp. 1590-1601
    • Enders, D.1    Grondai, C.2    Hüttl, M.R.M.3
  • 15
    • 33947198541 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 1570-1581;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 1570-1581
  • 19
  • 20
    • 33745211429 scopus 로고    scopus 로고
    • D. Enders, M. R. M. Hüttl, C. Grondai, G. Raabe, Nature 2006, 441, 861-863. See also;
    • a) D. Enders, M. R. M. Hüttl, C. Grondai, G. Raabe, Nature 2006, 441, 861-863. See also;
  • 22
    • 33846429586 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 467-469;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 467-469
  • 27
    • 34248192461 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 1101-1104;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 1101-1104
  • 29
    • 34447294558 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 4922-4925;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 4922-4925
  • 31
    • 36849071044 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 9050-9053;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 9050-9053
  • 33
    • 37349042884 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 9202-9205.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 9202-9205
  • 34
    • 54349110537 scopus 로고    scopus 로고
    • For the synthesis of compounds with quaternary stereocenters (three examples) by means of an organocatalytic sequential strategy, see reference [7c
    • For the synthesis of compounds with quaternary stereocenters (three examples) by means of an organocatalytic sequential strategy, see reference [7c].
  • 35
    • 34250669449 scopus 로고    scopus 로고
    • For a recent highlight on the impact of diarylprolinol ether 5 in asymmetric aminocatalysis, see: a
    • For a recent highlight on the impact of diarylprolinol ether 5 in asymmetric aminocatalysis, see: a) C. Palomo. A. Mielgo, Angew. Chem. 2006, 118, 8042-8046;
    • (2006) Angew. Chem , vol.118 , pp. 8042-8046
    • Palomo, C.1    Mielgo, A.2
  • 36
    • 33845505476 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7876-7880: see also reference [6]; for selected examples, see:
    • Angew. Chem. Int. Ed. 2006, 45, 7876-7880: see also reference [6]; for selected examples, see:
  • 39
    • 22144459070 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4212-4215;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 4212-4215
  • 40
    • 34548773182 scopus 로고    scopus 로고
    • for our contributions toward expansion of the scope of diarylprolinol ethers, see: d
    • for our contributions toward expansion of the scope of diarylprolinol ethers, see: d) A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Angew. Chem. 2007, 119, 4588-4590;
    • (2007) Angew. Chem , vol.119 , pp. 4588-4590
    • Carlone, A.1    Bartoli, G.2    Bosco, M.3    Sambri, L.4    Melchiorre, P.5
  • 41
    • 34250707214 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 4504-4506;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 4504-4506
  • 43
    • 34548764427 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 6882-6885.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 6882-6885
  • 44
    • 54349124033 scopus 로고    scopus 로고
    • It is impressive how, despite being the main component of one of the most used superglue solution (Loctite* Super Attak, Henkel), ethyl 2-cyanoacrylate 2a is compatible with organocatalytic reaction conditions. This underscores, once again, the reliability and the synthetic potential of asymmetric aminocatalysis.
    • It is impressive how, despite being the main component of one of the most used superglue solution (Loctite* Super Attak, Henkel), ethyl 2-cyanoacrylate 2a is compatible with organocatalytic reaction conditions. This underscores, once again, the reliability and the synthetic potential of asymmetric aminocatalysis.
  • 45
    • 54349097436 scopus 로고    scopus 로고
    • 2H) and basic additives (e.g., DABCO) resulted in considerably lower reaction rate and worse diastereoseleclivity.
    • 2H) and basic additives (e.g., DABCO) resulted in considerably lower reaction rate and worse diastereoseleclivity.
  • 46
    • 54349114617 scopus 로고    scopus 로고
    • Efforts to use aliphatic cyanoacrylate derivatives in the triple organocascade resulted in very poor conversion
    • Efforts to use aliphatic cyanoacrylate derivatives in the triple organocascade resulted in very poor conversion.
  • 47
    • 54349089804 scopus 로고    scopus 로고
    • Further studies toward the asymmetric preparation of enantiopure cyclohexanes having six stereocenters are underway
    • Further studies toward the asymmetric preparation of enantiopure cyclohexanes having six stereocenters are underway.
  • 48
    • 0037431283 scopus 로고    scopus 로고
    • For recent examples of this method to assign the absolute configurations of organic molecules, see: a
    • For recent examples of this method to assign the absolute configurations of organic molecules, see: a) C. Diedrich. S. Grimme, J. Phys. Chem. A 2003, 107, 2524-2539;
    • (2003) J. Phys. Chem. A , vol.107 , pp. 2524-2539
    • Diedrich, C.1    Grimme, S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.