Double nucleophilic addition to α,β-unsaturated aldimines induced by titanium tetrahalides

Tetrahedron Letters

Volumn 40, Issue 48, 1999, Pages 8401-8405

  Shimizu, Makoto ^a   Morita, Asato ^a   Kaga, Tomoyuki ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

, Unsaturated imine; Double nucleophilic addition; Titanium tetrahalide

Indexed keywords

ACETAL DERIVATIVE; CHEMICAL COMPOUND; IMINE; REAGENT; TITANIUM DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; REACTION ANALYSIS;

EID: 0033607442     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01794-3     Document Type: Article

References (18)

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15. 1H NMR. For cyclization into lactam. See, for example: (a) Shono, T.; Tsubata, K.; Okinaga, N. J. Org. Chem. 1984, 49, 1056. (b) Hattori, K.; Yamamoto, H. Synlett1993, 239.
16. 1H NMR. For cyclization into lactam. See, for example: (a) Shono, T.; Tsubata, K.; Okinaga, N. J. Org. Chem. 1984, 49, 1056. (b) Hattori, K.; Yamamoto, H. Synlett 1993, 239.
17. 4) and concentrated in vacuo to give a crude oil. Purification on silica gel TLC (n-hexane:ethyl acetate=20:1 as eluent) gave syn-1,4-1,2-adduct syn-6 (52.6 mg, 65%) and anti-6 (4.0 mg, 5%).
18. The AM1 and MNDO calculations were performed using MOPAC on CAChe®. Optimized structures were further characterized by the Hückel application.