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Volumn 10, Issue 18, 2008, Pages 3977-3980

Synthesis of N-allylideneamines and their use for the double nucleophilic addition of ketene silyl (thio)acetals and trimethylsilyl cyanide

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ACROLEIN; AMINE; CYANIDE; ETHYLENE DERIVATIVE; KETENE; KETONE; SILICON; TRIMETHYLSILYL CYANIDE; TRIMETHYLSILYL DERIVATIVE;

EID: 55949102066     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8014539     Document Type: Article
Times cited : (10)

References (45)
  • 15
    • 61349147556 scopus 로고    scopus 로고
    • Although we examined the 1,4- and 1,2-double nucleophilic addition using the imine 1 N-substituted with a TBS group, 1,4- and 1,2-double addition products were not obtained
    • Although we examined the 1,4- and 1,2-double nucleophilic addition using the imine 1 N-substituted with a TBS group, 1,4- and 1,2-double addition products were not obtained.
  • 16
    • 61349168213 scopus 로고    scopus 로고
    • When 1,4- and 1,2-double nucleophilic addition was carried out using the αβ-unsaturated inline having an electron-withdrawing group at the nitrogen, a 1,4-addition product was obtained instead of 1,4- and 1,2-adducts
    • When 1,4- and 1,2-double nucleophilic addition was carried out using the αβ-unsaturated inline having an electron-withdrawing group at the nitrogen, a 1,4-addition product was obtained instead of 1,4- and 1,2-adducts.
  • 27
    • 61349117824 scopus 로고    scopus 로고
    • For example, benzophenone was obtained from the reaction below, Chemical Equation Presented
    • For example, benzophenone was obtained from the reaction below. (Chemical Equation Presented)
  • 30
    • 61349098299 scopus 로고    scopus 로고
    • Calculations were carried out using the SPARTAN pro program and optimization with 6-3IG*.
    • Calculations were carried out using the SPARTAN pro program and optimization with 6-3IG*.
  • 31
    • 61349184167 scopus 로고    scopus 로고
    • The difference in the method of calculation (HF/STO-3G, and PM3) has little influence on a qualitative conclusion.
    • The difference in the method of calculation (HF/STO-3G, and PM3) has little influence on a qualitative conclusion.
  • 32
    • 33746310614 scopus 로고    scopus 로고
    • 2O, Amberlyst 15DRY, and Florisil gave 1,4- and 1,2-addition products 2aa in low yields. The amount and the shape of silica gel were also examined. See the Supporting Information. Examples using silica gel as a reaction promoter, see: Shimizu, M.; Tanaka, M.; Itoh, T.; Hachiya, I. Synlett 2006, 1687.
    • 2O, Amberlyst 15DRY, and Florisil gave 1,4- and 1,2-addition products 2aa in low yields. The amount and the shape of silica gel were also examined. See the Supporting Information. Examples using silica gel as a reaction promoter, see: Shimizu, M.; Tanaka, M.; Itoh, T.; Hachiya, I. Synlett 2006, 1687.
  • 33
    • 61349135235 scopus 로고    scopus 로고
    • 1H NMR that 1,4-1,2-adduct products 2a were changed to 1,4-adducts via retro-Strecker reaction (Table 1, entries 3, 4, 6). Since the adducts were not stable, the addition reactions were not examined with 1a in detail (Table 1, entries 8-11).
    • 1H NMR that 1,4-1,2-adduct products 2a were changed to 1,4-adducts via retro-Strecker reaction (Table 1, entries 3, 4, 6). Since the adducts were not stable, the addition reactions were not examined with 1a in detail (Table 1, entries 8-11).
  • 44
    • 33748661764 scopus 로고    scopus 로고
    • Regioselectivity on the addition of nucleophiles to αβ- unsaturated aldimimes has been studied previously, see ref 4c. Examples using αβ-unsaturated aldimimes for the β-lactam synthesis, see: (a) Fleming, I, Kilburn, J. D. J. Chem. Soc, Perkin Trans. 1 1998, 2663
    • Regioselectivity on the addition of nucleophiles to αβ- unsaturated aldimimes has been studied previously, see ref 4c. Examples using αβ-unsaturated aldimimes for the β-lactam synthesis, see: (a) Fleming, I.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 1998, 2663.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.