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Volumn 68, Issue 26, 2003, Pages 10187-10190

Synthesis of Enantiomerically Enriched Oxazolinyl[1,2]Oxazetidines

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOMERIC MIXTURES; OPTICAL ACTIVITY;

EID: 0345731478     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035360u     Document Type: Article
Times cited : (32)

References (26)
  • 8
    • 0347691523 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy in the crude reaction mixture.
  • 9
    • 0347060821 scopus 로고    scopus 로고
    • note
    • The alkenyloxazoline 6 was assigned the E configuration by analogy to what was reported in the case of similar alkenyloxazolines (see ref 4).
  • 10
    • 0347060819 scopus 로고    scopus 로고
    • note
    • The relative configuration of the spirocyclic compound 7 was simply ascertained by a NOESY experiment.
  • 11
    • 0001449812 scopus 로고
    • CH coupling constant (in the range 2.8-3.3 Hz) with respect to 5d (5.7 Hz) having both these groups in cis, thus validating this spectroscopic relationship also in the case of this kind of heterocycles.
    • (1978) J. Org. Chem. , vol.43 , pp. 4696-4700
    • Kingsbury, C.A.1    Durham, D.L.2    Hutton, R.3
  • 15
    • 0035903912 scopus 로고    scopus 로고
    • and ref therein
    • (d) Merino, P.; Tejero, T. Tetrahedron 2001, 57, 8125-8128 and ref. therein.
    • (2001) Tetrahedron , vol.57 , pp. 8125-8128
    • Merino, P.1    Tejero, T.2
  • 19
    • 0347060820 scopus 로고    scopus 로고
    • note
    • CCDC-215912 contains the supplementary crystallographic data for compound (-)-10c. These data can be obtained free of charge at www.ccdc.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK. Fax: (int) +44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk.
  • 20
    • 0000170732 scopus 로고
    • Following a reported experimental procedure (see: Pirkle, W. H.; Rinaldi, P. L. J. Org. Chem. 1977, 42, 3217-3219) applied to N-tert-butyloxaziridines, racemic oxazolinyl[1,2]oxazetidines 10a-c (prepared starting from racemic valinol) were found to split in the presence of the above-cited CSA in correspondence of the t-Bu group and the oxazetidine ring hydrogen. The ee values found were >96%.
    • (1977) J. Org. Chem. , vol.42 , pp. 3217-3219
    • Pirkle, W.H.1    Rinaldi, P.L.2
  • 21
    • 0345799518 scopus 로고    scopus 로고
    • note
    • A very poor stereoselectivity was also encountered in the reaction of lithiated optically active 2-(1-chloroethyl)-4-methoxymethyl-5-phenyl-2-oxazoline with carbonyl compounds (see ref 13).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.