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Volumn 69, Issue 26, 2013, Pages 5331-5341

Palladium-catalyzed highly regio- and stereoselective carbon-carbon bond formation reaction of γ-substituted vinylaziridines with a silylated masked acyl cyanide reagent

Author keywords

Aziridine Allyl complex; Masked acyl cyanide; Palladium

Indexed keywords

ACYL CYANIDE REAGENT; BENZYL CYANIDE DERIVATIVE; CARBON; PALLADIUM COMPLEX; TERT BUTYLDIMETHYLSILYL; UNCLASSIFIED DRUG; VINYLAZIRIDINE DERIVATIVE;

EID: 84878262619     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.04.129     Document Type: Article
Times cited : (11)

References (40)
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    • B.M. Trost, I. Flemming, Pergamon New York, NY Chapter 3.3
    • S.A. Godleski B.M. Trost, I. Flemming, Comprehensive Organic Synthesis Vol. 4 1991 Pergamon New York, NY Chapter 3.3
    • (1991) Comprehensive Organic Synthesis , vol.4
    • Godleski, S.A.1
  • 8
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    • 3-allylpalladium complex
    • 3-allylpalladium complex
  • 14
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    • Preparation of 3
    • Preparation of 3
  • 17
    • 67650044561 scopus 로고    scopus 로고
    • Protected Dicyanomethanol (H-MAC-R)
    • H-MAC-Ac has been commercially available from Sigma-Aldrich since 2013
    • H. Nemoto Protected Dicyanomethanol (H-MAC-R) Electronic Encyclopedia of Reagents for Organic Synthesis (e-EROS) 2007: http://onlinelibrary.wiley.com/o/ eros/articles/rn00761/frame.html H-MAC-Ac has been commercially available from Sigma-Aldrich since 2013
    • (2007) Electronic Encyclopedia of Reagents for Organic Synthesis (E-EROS)
    • Nemoto, H.1
  • 19
    • 0000802637 scopus 로고
    • When a non-strained (not highly reactive) leaving group, such as an alkoxycarbonyl was used, 4 was not effective because the nucleophilicity of a Pd-phosphite complex is generally weaker than that of a phosphine complex. However, 4-methyl-3,5,8-trioxa-1-phosphabicyclo[2.2.2]octane (A), a tricyclic phosphine ligand, was effective
    • When a non-strained (not highly reactive) leaving group, such as an alkoxycarbonyl was used, 4 was not effective because the nucleophilicity of a Pd-phosphite complex is generally weaker than that of a phosphine complex. However, 4-methyl-3,5,8-trioxa-1-phosphabicyclo[2.2.2]octane (A), a tricyclic phosphine ligand, was effective: T. Takahashi, Y. Jinbo, K. Kitamura, and J. Tsuji Tetrahedron Lett. 25 1984 5921 5924
    • (1984) Tetrahedron Lett. , vol.25 , pp. 5921-5924
    • Takahashi, T.1    Jinbo, Y.2    Kitamura, K.3    Tsuji, J.4
  • 23
    • 0002462212 scopus 로고    scopus 로고
    • Sweeney et al. mainly reported the reaction of vinylaziridines with copper reagents. Thus, the detail of the palladium-catalyzed reaction, such as mol % of tetrakis(triphenylphosphine)palladium, temperature, or equivalents of diethyl malonate were not specified
    • Sweeney et al. mainly reported the reaction of vinylaziridines with copper reagents. Thus, the detail of the palladium-catalyzed reaction, such as mol % of tetrakis(triphenylphosphine)palladium, temperature, or equivalents of diethyl malonate were not specified: A.A. Cantrill, N.A. Jarvis, I.M. Osborn, A. Ouadi, and B.J. Sweeney Synlett 1996 847 849
    • (1996) Synlett , pp. 847-849
    • Cantrill, A.A.1    Jarvis, N.A.2    Osborn, I.M.3    Ouadi, A.4    Sweeney, B.J.5
  • 24
    • 84878239515 scopus 로고    scopus 로고
    • Synthetic application of a MAC reagent with palladium catalyst in high γ-selectivity according to Ref. 5 was reported. They mentioned that the unmasking step from the MAC moiety to carbonyl functionality proceeded in greater yield under milder conditions than the step for the acidic hydrolysis of the cyanide group
    • Synthetic application of a MAC reagent with palladium catalyst in high γ-selectivity according to Ref. 5 was reported. They mentioned that the unmasking step from the MAC moiety to carbonyl functionality proceeded in greater yield under milder conditions than the step for the acidic hydrolysis of the cyanide group
  • 27
    • 84878221678 scopus 로고    scopus 로고
    • Active methylene and methyne compounds bearing a cyano group as an electron withdrawing group are known to be very palladium-affinitive nucleophiles
    • Active methylene and methyne compounds bearing a cyano group as an electron withdrawing group are known to be very palladium-affinitive nucleophiles
  • 32
    • 84878217294 scopus 로고    scopus 로고
    • 2 moiety is not highly acidic. Furthermore, they only examined triphenylphosphine but not 4.
    • 2 moiety is not highly acidic. Furthermore, they only examined triphenylphosphine but not 4.
  • 33
    • 84878217426 scopus 로고    scopus 로고
    • 2 (MAC reagents), which are smaller than 2-methylmalononitrile. Incidentally, the smallest active methyne must be hydrogen cyanide
    • 2 (MAC reagents), which are smaller than 2-methylmalononitrile. Incidentally, the smallest active methyne must be hydrogen cyanide.
  • 35
    • 84878221268 scopus 로고    scopus 로고
    • Although very high stereoselectivity was observed, the double inversion mechanism has been generally accepted. Therefore, the proposed mechanism for stereochemistry is illustrated in Supplementary data in order to focus the discussion on the regiochemistry
    • Although very high stereoselectivity was observed, the double inversion mechanism has been generally accepted. Therefore, the proposed mechanism for stereochemistry is illustrated in Supplementary data in order to focus the discussion on the regiochemistry.
  • 39
    • 84878238619 scopus 로고    scopus 로고
    • 1H data for 15g-15j and 16g-16j, are available in Supplementary data
    • 1H data for 15g-15j and 16g-16j, are available in Supplementary data.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.