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Volumn 70, Issue 10, 2005, Pages 4142-4151

Ketone-imide versus ketone-oxime reductive cross-coupling promoted by samarium diiodide: New mechanistic insight gained from a failed aminocyclopentitol synthesis

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS; KETONES; MATHEMATICAL MODELS; QUANTUM THEORY; SUBSTRATES;

EID: 18744374182     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050185y     Document Type: Article
Times cited : (25)

References (61)
  • 30
    • 18744367932 scopus 로고    scopus 로고
    • note
    • We had successfully used previously our one-pot oxidation-reductive coupling protocol for the carbocyclization of a closely related keto-aldehyde derived from D-glucosamine protected as N-acetamide or as N-t-Boc carbamate.
  • 44
    • 18744402009 scopus 로고    scopus 로고
    • note
    • 13C) and 2D NMR (DQ-COSY, NOESY, HSQC, and HMBC) experiments (see the Supporting Information).
  • 46
    • 18744381400 scopus 로고    scopus 로고
    • note
    • 6a for the intermolecular pinacol coupling reaction between W-acyl lactams and carbonyl compounds. However, these authors favor the formation of an acyl radical intermediate, which is subsequently reduced to a transient acyl samarium species.
  • 47
    • 18744382596 scopus 로고    scopus 로고
    • note
    • 21 have shown that oxime ethers are not electrochemically reducible under the same conditions as they are coupled to ketones, which led them to propose the intermediacy of ketyl radical-anions for the corresponding electrochemical cross-coupling.
  • 51
    • 18744415826 scopus 로고    scopus 로고
    • Chem. Abs. 75: 129147
    • Chem. Abs. , vol.75 , pp. 129147
  • 54
    • 0037187138 scopus 로고    scopus 로고
    • We employed the strategy of using a relatively large basis set but without diffuse functions, which confines the excess electron to the molecular framework allowing relative estimates for molecules with negative valence electron affinities using the DFT method: (a) Li, Y.; Cai, Z.; Sevilla, M. D. J. Phys. Chem. A 2002, 106, 1596-1603.
    • (2002) J. Phys. Chem. A , vol.106 , pp. 1596-1603
    • Li, Y.1    Cai, Z.2    Sevilla, M.D.3
  • 57
    • 0036025403 scopus 로고    scopus 로고
    • By convention, a positive EA indicates that the binding reaction of a neutral molecule with an electron is an exoergic process. For a recent review on electron affinity covering theoretical computations, see: Rienstra-Kiracofe, J.; Tschumper, G. S.; Schaefer, H. F., III; Nandi, S.; Ellison, G. B. Chem. Rev. 2002, 102, 231-282.
    • (2002) Chem. Rev. , vol.102 , pp. 231-282
    • Rienstra-Kiracofe, J.1    Tschumper, G.S.2    Schaefer III, H.F.3    Nandi, S.4    Ellison, G.B.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.