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Volumn 73, Issue 22, 2008, Pages 9188-9191

Zinc-mediated allylation and alkylation of aminals in the presence of TMSCl and diisopropylamine

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; HYDROCARBONS; ORGANOMETALLICS; ZINC;

EID: 56449092685     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8019797     Document Type: Article
Times cited : (24)

References (27)
  • 2
    • 56449116177 scopus 로고    scopus 로고
    • Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Flemingl., Eds.; Pergamon: Oxford, UK, 1991; 1, pp 211-229.
    • (b) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Flemingl., Eds.; Pergamon: Oxford, UK, 1991; Vol 1, pp 211-229.
  • 4
    • 56449100270 scopus 로고    scopus 로고
    • Rathke, M. W., Weipert, P. In Comprehensive Organic Synthesis; Trost, B. M., Flemingl., Eds.; Pergamon: Oxford, UK, 1991 ; 1, pp 277-299.
    • (b) Rathke, M. W., Weipert, P. In Comprehensive Organic Synthesis; Trost, B. M., Flemingl., Eds.; Pergamon: Oxford, UK, 1991 ; Vol. 1, pp 277-299.
  • 6
    • 33344464799 scopus 로고    scopus 로고
    • References for acetals using Barbier- and Reformatsky-type reaction, see: a
    • References for acetals using Barbier- and Reformatsky-type reaction, see: (a) Surendra, K.; Krishnaveni, N. S.; Rao, K. R. Tetrahedron Lett. 2006, 47, 2133-2136.
    • (2006) Tetrahedron Lett , vol.47 , pp. 2133-2136
    • Surendra, K.1    Krishnaveni, N.S.2    Rao, K.R.3
  • 11
    • 13844266386 scopus 로고    scopus 로고
    • References for aminals and related compounds using Barbier- and Reformatsky-type reaction, see: a
    • References for aminals and related compounds using Barbier- and Reformatsky-type reaction, see: (a) Katritzky, A. R.; Manju, K.; Singh, S. K.; Meher, N. K. Tetrahedron 2005, 61, 2555-2581.
    • (2005) Tetrahedron , vol.61 , pp. 2555-2581
    • Katritzky, A.R.1    Manju, K.2    Singh, S.K.3    Meher, N.K.4
  • 15
    • 0037189263 scopus 로고    scopus 로고
    • For recently selected examples using Barbier- and Reformatsky-type reaction, see: a
    • For recently selected examples using Barbier- and Reformatsky-type reaction, see: (a) Petrini, M.; Profeta, R.; Right, P. J. Org. Chem. 2002, 67, 4530-4535.
    • (2002) J. Org. Chem , vol.67 , pp. 4530-4535
    • Petrini, M.1    Profeta, R.2    Right, P.3
  • 19
    • 56449130397 scopus 로고    scopus 로고
    • The silylated amines (N-trimethylsilylpiperidine and N-trimethylsilyldiisopropylamine) and allylated piperidine (3-piperidino-1-propene) were observed by GC-MS, which were removed by hydrolysis and evaporation. In contrast, allylated diisopropylamine was not observed.
    • The silylated amines (N-trimethylsilylpiperidine and N-trimethylsilyldiisopropylamine) and allylated piperidine (3-piperidino-1-propene) were observed by GC-MS, which were removed by hydrolysis and evaporation. In contrast, allylated diisopropylamine was not observed.
  • 20
    • 37049081144 scopus 로고    scopus 로고
    • Aminals (1i and 1j) were prepared according to a modified procedure of a known method, see: Katritzky, A. R.; Drewniak, M. J. Chem. Soc., Perkin Trans. 1 1988, 2339-2344.
    • Aminals (1i and 1j) were prepared according to a modified procedure of a known method, see: Katritzky, A. R.; Drewniak, M. J. Chem. Soc., Perkin Trans. 1 1988, 2339-2344.
  • 21
    • 56449112504 scopus 로고    scopus 로고
    • 1H NMR of crude product.
    • 1H NMR of crude product.
  • 26
    • 56449114031 scopus 로고    scopus 로고
    • In previous reports, butaverine was obtained by Michael addition of piperidine to n-propyl cinnamate in 20-50% yields, see ref 11
    • In previous reports, butaverine was obtained by Michael addition of piperidine to n-propyl cinnamate in 20-50% yields, see ref 11.
  • 27
    • 22244458282 scopus 로고    scopus 로고
    • Preparation of butyl α-bromoacetate, see
    • Preparation of butyl α-bromoacetate, see: Zhu, X.-F.; Schaffrer, A.-P.; Li, R. C.; Kwon, O. Org. Lett. 2005, 7, 2977-2980.
    • (2005) Org. Lett , vol.7 , pp. 2977-2980
    • Zhu, X.-F.1    Schaffrer, A.-P.2    Li, R.C.3    Kwon, O.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.