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Volumn 53, Issue 44, 2012, Pages 5903-5906

Double nucleophilic N-alkylation of α-oxime-esters with Grignard reagents

Author keywords

Amino acid; Cascade reaction; Electrophilic amination; Oxime; Umpolung

Indexed keywords

ALPHA OXIME; DIETHYLZINC; ESTER DERIVATIVE; GRIGNARD REAGENT; OXIME DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84866756027     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.08.091     Document Type: Article
Times cited : (18)

References (29)
  • 13
    • 20444400592 scopus 로고    scopus 로고
    • Svete et al.
    • Svete et al. reported double N-alkylation with unprotected oxime-ester and large excess Grignard reagents. To the best of our knowledge, this is the sole example. See: U. Grošelj, D. Bevk, R. Jakše, A. Meden, B. Stanovnik, and J. Svete Tetrahedron: Asymmetry 16 2005 2187 2197
    • (2005) Tetrahedron: Asymmetry , vol.16 , pp. 2187-2197
    • Grošelj, U.1    Bevk, D.2    Jakše, R.3    Meden, A.4    Stanovnik, B.5    Svete, J.6
  • 18
    • 84866749894 scopus 로고    scopus 로고
    • PCT Int. Appl. WO/2011/093423
    • For selective preparation of (E)-oxime, see: Moriyama, N.; Kobayashi, R. PCT Int. Appl. WO/2011/093423.
    • Moriyama, N.1    Kobayashi, R.2
  • 19
    • 84866771497 scopus 로고    scopus 로고
    • E/Z chemistry of starting materials was determined by X-ray crystallographic analysis. Deposited Crystallographic data for 1a, 1i, and 3a with the Cambridge Crystallographic Data Center are as follows: CCDC 871698, 871699, and 872157. These crystallographic information can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK; fax: +44 1223 336 033; or via. See also Supplementary data.
    • E/Z chemistry of starting materials was determined by X-ray crystallographic analysis. Deposited Crystallographic data for 1a, 1i, and 3a with the Cambridge Crystallographic Data Center are as follows: CCDC 871698, 871699, and 872157. These crystallographic information can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK; fax: +44 1223 336 033; or via http://www.ccdc.cam.ac.uk/ conts/retrieving.html. See also Supplementary data.
  • 26
    • 84862201298 scopus 로고    scopus 로고
    • Very recently, Fujioka et al.
    • Very recently, Fujioka et al. reported reactions with 3-alkoxycarbonylisoxazoles and methyl and aryl Grignard reagents, which produced C-substituted compounds. See: K. Murai, S. Miyazaki, and H. Fujioka Tetrahedron Lett. 53 2012 3746 3749
    • (2012) Tetrahedron Lett. , vol.53 , pp. 3746-3749
    • Murai, K.1    Miyazaki, S.2    Fujioka, H.3
  • 27
    • 84866771498 scopus 로고    scopus 로고
    • Abstract 1 K6-15, Mar 25
    • Shimizu et al. also recently reported cascade and sequential N,N-double alkylation of sulfoximinoester using alkyl Grignard reagents in toluene. See: Hata, S.; Shimizu, M. Abstract, 92nd Annual Meeting of the Chemical Society of Japan, 1 K6-15, Mar 25, 2012.
    • (2012) 92nd Annual Meeting of the Chemical Society of Japan
    • Hata, S.1    Shimizu, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.