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Volumn 6, Issue 6, 2006, Pages 649-651

Rapid generation of molecular complexity using "hybrid" multi-component reactions (MCRs): Application to the synthesis of α-amino nitriles and 1,2-diamines

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; CARBON; DIAMINE DERIVATIVE; NITRILE; PIPERIDINE DERIVATIVE;

EID: 33646024002     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b516192d     Document Type: Article
Times cited : (17)

References (43)
  • 1
    • 84890597202 scopus 로고    scopus 로고
    • (Eds.:, J. Zhu, H. Bienaymé), Wiley-VCH, Weinheim, Germany, For recent reviews, see:
    • Multicomponent Reactions (Eds.:, J. Zhu, H. Bienaymé,), Wiley-VCH, Weinheim, Germany, 2005
    • (2005) Multicomponent Reactions
  • 12
    • 0041378065 scopus 로고    scopus 로고
    • and references therein
    • H. Groger Chem. Rev. 2003 103 2795
    • (2003) Chem. Rev. , vol.103 , pp. 2795
    • Groger, H.1
  • 25
  • 38
    • 3042816129 scopus 로고    scopus 로고
    • and references cited therein The concept of combining two or more MCRs to increase the number of reaction components that can be brought together in a single vessel has been demonstrated previously. For a remarkable 7-CR based upon this idea, see:
    • J. J. Shiers M. Shipman J. F. Hayes A. M. Z. Slawin J. Am. Chem. Soc. 2004 126 6868
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 6868
    • Shiers, J.J.1    Shipman, M.2    Hayes, J.F.3    Slawin, A.M.Z.4
  • 39
    • 33748223166 scopus 로고
    • α-Amino nitrile 2 readily loses HCN reverting to the ketimine (and hence ketone). The lability of Strecker products derived from ketimines has been noted previously, see, for example:
    • A. Dömling I. Ugi Angew. Chem., Int. Ed. 1993 32 563
    • (1993) Angew. Chem., Int. Ed. , vol.32 , pp. 563
    • Dömling, A.1    Ugi, I.2
  • 41
    • 33646075358 scopus 로고    scopus 로고
    • note
    • int = 0.0747], R [I > 2σ(I)] = 0.0772, wR [I > 2σ(I)] = 0.1880, GooF = 1.012. The asymmetric unit of the cyclic urea derivative of 6 contains two crystallographically independent but chemically identical molecules. CCDC 286809. For crystallographic data in CIF or other electronic format see DOI: 10.1039/b516192d
  • 43
    • 33646069866 scopus 로고    scopus 로고
    • This assignment is based on our earlier synthesis of (+)-coniine from (S)-14 (ref. 10b), wherein hydride was observed to add to the Re face of the presumed intermediate iminium cation. Assuming cyanide attack occurs via the same Re face, the (S)-configuration is expected at C-2
    • This assignment is based on our earlier synthesis of (+)-coniine from (S)-14 (ref. 10b), wherein hydride was observed to add to the Re face of the presumed intermediate iminium cation. Assuming cyanide attack occurs via the same Re face, the (S)-configuration is expected at C-2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.