메뉴 건너뛰기




Volumn 69, Issue 24, 2004, Pages 8485-8488

New C-C coupling reaction of cyclic nitronates with carbon nucleophiles. Umpolung of the conventional reactivity of nitronates

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYSTS; NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY;

EID: 9344263481     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048944k     Document Type: Article
Times cited : (42)

References (31)
  • 8
    • 0001673687 scopus 로고
    • N,N-Bis(hydroxy)iminium cations are widely discussed as intermediates of the Nef reaction: Kornblum, N.; Brown, R. A. J. Am. Chem. Soc. 1965, 87, 1742.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 1742
    • Kornblum, N.1    Brown, R.A.2
  • 9
    • 9344269754 scopus 로고    scopus 로고
    • ref 2d
    • For the suggested generation of 2 by silylation of silylnitronates, see: (a) ref 2d.
  • 16
    • 0001053365 scopus 로고    scopus 로고
    • Compounds 1a-j were prepared from nitromethane or nitroethane using the modified procedures of the following: (a) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137.
    • (1996) Chem. Rev. , vol.96 , pp. 137
    • Denmark, S.E.1    Thorarensen, A.2
  • 19
    • 9344220294 scopus 로고    scopus 로고
    • note
    • The NMR investigation of the N,N-bis(oxy)iminium cations formed upon the interaction of TBDMSOTf with other nitronates will be published in due course.
  • 20
    • 0030923304 scopus 로고    scopus 로고
    • The electrophilicity parameter (E) for N,N-dialkyliminium cations is ca. -5: Mayr, H.; Ofial, A. R. Tetrahedron Lett. 1997, 3503. It might be expected that the E parameter for cations 2 is higher.
    • (1997) Tetrahedron Lett , pp. 3503
    • Mayr, H.1    Ofial, A.R.2
  • 21
    • 0037363116 scopus 로고    scopus 로고
    • For catalytic activation of electrophilic reagents with silicon Lewis acids, see: Dilman, A. D.; Ioffe, S. L. Chem. Rev. 2003, 103, 733.
    • (2003) Chem. Rev. , vol.103 , pp. 733
    • Dilman, A.D.1    Ioffe, S.L.2
  • 22
    • 9344240240 scopus 로고    scopus 로고
    • note
    • 1H NMR data of crude reaction mixtures did not reveal the presence of the diastereomers, except those shown in Table 2. (13) The N-attack of carbenium cations on enamines can be characterized by a rate higher than that of the C-attack (for the discussion, see ref 10 and references therein). Normally, N-vinylammonium cations are thermodynamically less stable than the isomeric iminium ions (i.e., the products resulted from C-attack). Therefore, N-alkylated enamine 9 could be formed as a kinetic product, which cannot rearrange to the iminium cation like 8 due to the fast irreversible loss of the silyl group.
  • 25
    • 9344224337 scopus 로고    scopus 로고
    • CCDC 230273 (4d), CCDC 230274 (4c), CCDC 230275 (4f), CCDC 230276 (10), CCDC 230277 (4g″), and CCDC 230278 (4j) contain the supplementary crystallographic data for this paper. These data can be obtained online (http://www.ccdc.cam.ac.uk/cgi-bin/catreq.cgi) free of charge.
  • 27
    • 0000639932 scopus 로고
    • For data on the hindered inversion of the nitrogen atom in the systems bearing the O-N-O fragment, see: Rudchenko, V. F. Chem. Rev. 1993, 93, 725.
    • (1993) Chem. Rev. , vol.93 , pp. 725
    • Rudchenko, V.F.1
  • 28
    • 9344246662 scopus 로고    scopus 로고
    • note
    • N processes in oxazine derivatives, see ref 14b.
  • 30
    • 9344228259 scopus 로고    scopus 로고
    • note
    • Alternatively, the generation of 4e′-g′, along with 4e-g, could be explained as a result of the competition between syn and anti approaches of 3 relative to C-6 of the cationic intermediate 2 (cf. ref 19).
  • 31
    • 9344239140 scopus 로고    scopus 로고
    • note
    • The prepared tetrahydrooxazine derivatives 4a-j, 6, 8, 10, and 13 could be considered structural analogues to the well-known N- trialkylsiloxyisoxazolidines. (For preparation of natural and biologically active compounds from N-trialkylsiloxyisoxazolidines, see ref 1b.)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.