메뉴 건너뛰기




Volumn , Issue 18, 2000, Pages 3229-3233

Novel Me3Si-mediated intramolecular cyclisation/[4 + 2] cyclofragmentation of β-substituted γ-nitro ketones

Author keywords

Bond activation; Cyclic nitronic esters; Cycloadditions; Ketones; , Unsaturated oxime derivatives

Indexed keywords

2 TRIMETHYLSILYLOXY 2H [1,2]OXAZINE; KETONE DERIVATIVE; NITRO DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033799394     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200009)2000:18<3229::AID-EJOC3229>3.0.CO;2-M     Document Type: Article
Times cited : (16)

References (38)
  • 2
    • 0011200604 scopus 로고    scopus 로고
    • Engl. transl.
    • S. L. Ioffe, I. M. Lyapkalo, L. M. Makarenkova, J. Org. Chem. Russ. 1998, 34, 1141-1148 (Russ.); Russ. J. Org. Chem. 1998, 34, 1085-1092 (Engl. transl.)
    • (1998) Russ. J. Org. Chem. , vol.34 , pp. 1085-1092
  • 3
    • 0007154217 scopus 로고
    • (Ed.: L. Paquette) Wiley, New York
    • For an early short review article devoted to the chemistry of N,N-bis(lithioxy)enamines (so-called "superenamines"), see: R. E. Marti, D. Seebach, Encyclopedia of Reagents for Organic Synthesis, (Ed.: L. Paquette) Wiley, New York, 1995, 3, 1946-1948; Encyclopedia of Reagents for Organic Synthesis, (Ed.: L. Paquette) Wiley, New York, 1995, 5, 3551-3552.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.3 , pp. 1946-1948
    • Marti, R.E.1    Seebach, D.2
  • 4
    • 0342340918 scopus 로고
    • (Ed.: L. Paquette) Wiley, New York
    • For an early short review article devoted to the chemistry of N,N-bis(lithioxy)enamines (so-called "superenamines"), see: R. E. Marti, D. Seebach, Encyclopedia of Reagents for Organic Synthesis, (Ed.: L. Paquette) Wiley, New York, 1995, 3, 1946-1948; Encyclopedia of Reagents for Organic Synthesis, (Ed.: L. Paquette) Wiley, New York, 1995, 5, 3551-3552.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.5 , pp. 3551-3552
  • 5
    • 0343798567 scopus 로고
    • For the synthesis and reactivity of N,N-bis(trialkylsilyloxy)enamines (BENA), see: [3a] H. Feger, G. Simchen, Liebigs Ann. 1986, 1456-1465.
    • (1986) Liebigs Ann. , pp. 1456-1465
    • Feger, H.1    Simchen, G.2
  • 13
    • 4043110175 scopus 로고
    • Engl. transl.
    • [5b] V. M. Danilenko, S. L. Ioffe, Yu. A. Strelenko, N. F. Karpenko, A. V. Kalinin, V. A. Tartakovsky, Bull. Acad. Sci. USSR. Div. Chem. Sci. 1987, 2638-2639 (Russ.); 1987, 2453-2454 (Engl. transl.).
    • (1987) Bull. Acad. Sci. USSR. Div. Chem. Sci. , pp. 2453-2454
  • 15
    • 21444435981 scopus 로고
    • Engl. transl.
    • [5c] S. L. Ioffe, V. M. Danilenko, Yu. A. Strelenko, V. A. Tartakovsky, J. Org. Chem. Russ. 1995, 31, 1253-1254 (Russ.); Russ. J. Org. Chem. 1995, 31, 1144-1145 (Engl. transl.).
    • (1995) Russ. J. Org. Chem. , vol.31 , pp. 1144-1145
  • 21
    • 1542794772 scopus 로고
    • 3SiOTf has been reported to be ineffective in promoting the addition of silyl enol ethers to regular nitro alkenes: A. Yoshikoshi, M. Miyashita, Acc. Chem Res. 1985, 18, 284-290.
    • (1985) Acc. Chem Res. , vol.18 , pp. 284-290
    • Yoshikoshi, A.1    Miyashita, M.2
  • 22
    • 0001053365 scopus 로고    scopus 로고
    • Recently, 5,6-dihydro-4H-[1,2]oxazine-2-oxides were systematically studied and widely applied as 1,3-dipoles in highly stereo-selective [3 + 2] cycloadditions to C-C double bonds: [11a] S. E. Denmark, A. Thorarensen, Chem. Rev. 1996, 96, 137-165.
    • (1996) Chem. Rev. , vol.96 , pp. 137-165
    • Denmark, S.E.1    Thorarensen, A.2
  • 25
    • 0342927508 scopus 로고    scopus 로고
    • note
    • β-H bond in the open-chain analogue A.
  • 30
    • 0343798565 scopus 로고    scopus 로고
    • note
    • We consider 5,6-dihydro-2-trimethylsilyloxy-2H-[1,2]oxazines of type C to be essentially less stable than their 5,6-dihydro-2-alkyl-or 5,6-dihydro-2-trialkylsilyl-analogues due to the destabilizing effect of the three heteroatoms in the O-N-O fragment. This effect may complicate their isolation or even observation by NMR spectroscopy.
  • 31
    • 0342927507 scopus 로고    scopus 로고
    • note
    • 3 group in both isomers of 9 was not determined, but it is equal according to NMR spectroscopic data.
  • 33
    • 0342493343 scopus 로고    scopus 로고
    • note
    • [5d]).
  • 34
    • 0342493344 scopus 로고    scopus 로고
    • note
    • 2. The summarized results will be published in due course.
  • 37
    • 0342493345 scopus 로고    scopus 로고
    • note
    • 3N in DMF in the conditions specified for butan-2-one in ref.[22]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.