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Volumn 9, Issue 17, 2007, Pages 3295-3298

Regio- and stereoselective lithiation of terminal oxazolinylaziridines: The aziridine N-substituent and the oxazolinyl group effect

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; LACTONE; LITHIUM; OXAZOLE DERIVATIVE;

EID: 34548192017     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071264u     Document Type: Article
Times cited : (24)

References (31)
  • 1
    • 0001318042 scopus 로고    scopus 로고
    • (a) Satoh, T. Chem. Rev. 1996, 96, 3303-3325.
    • (1996) Chem. Rev , vol.96 , pp. 3303-3325
    • Satoh, T.1
  • 3
    • 0242475011 scopus 로고    scopus 로고
    • For a special issue on Oxiranyl and Aziridinyl Anions (Florio, S. Ed.), see: Florio, S. Tetrahedron 2003, 59, 9693.
    • (c) For a special issue on Oxiranyl and Aziridinyl Anions (Florio, S. Ed.), see: Florio, S. Tetrahedron 2003, 59, 9693.
  • 21
    • 34548162106 scopus 로고    scopus 로고
    • 8 on aziridine 3a revealed only one set of signals for the aziridine protons in the range 293-195 K.
    • 8 on aziridine 3a revealed only one set of signals for the aziridine protons in the range 293-195 K.
  • 25
    • 0000136570 scopus 로고    scopus 로고
    • 3JHH coupling constants between the two aziridinyl protons ranging from 5.5 to 7.0 Hz, (see Supporting Information); see also: Yonezawa, T.; Morishima, I. J. Mol. Spectrom. 1968, 27, 210-217.
    • 3JHH coupling constants between the two aziridinyl protons ranging from 5.5 to 7.0 Hz, (see Supporting Information); see also: Yonezawa, T.; Morishima, I. J. Mol. Spectrom. 1968, 27, 210-217.
  • 26
    • 34548185653 scopus 로고    scopus 로고
    • In two cases (6a and 6b), the configuration of the major diastereomer was unambiguously determined by further conversion into 7a,b whose stereochemistry was deduced by NMR analysis (vide infra).
    • In two cases (6a and 6b), the configuration of the major diastereomer was unambiguously determined by further conversion into 7a,b whose stereochemistry was deduced by NMR analysis (vide infra).
  • 30
    • 34548185156 scopus 로고    scopus 로고
    • Compounds 8b and 9b were isolated in 18 and 36% yield, respectively. The reaction with PhCHO gave 8c in 22% yield as 1:1 mixture of diastereomers and 9c in 44% yield as a single diastereomer whose stereochemistry, at the newly created stereogenic centre, has not been determined yet.
    • Compounds 8b and 9b were isolated in 18 and 36% yield, respectively. The reaction with PhCHO gave 8c in 22% yield as 1:1 mixture of diastereomers and 9c in 44% yield as a single diastereomer whose stereochemistry, at the newly created stereogenic centre, has not been determined yet.
  • 31
    • 34548168566 scopus 로고    scopus 로고
    • 1H NMR spectra.
    • 1H NMR spectra.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.