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Volumn 128, Issue 36, 2006, Pages 11754-11755

Rhodium-catalyzed stereoselective formation of Z-enamines from allylaziridines

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ALLYLAZIRIDINE; AZIRIDINE DERIVATIVE; ENAMINE; RHODIUM; UNCLASSIFIED DRUG;

EID: 33748493781     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0632557     Document Type: Article
Times cited : (26)

References (33)
  • 3
    • 0004201576 scopus 로고    scopus 로고
    • Baldwin, J., Williams, R. M., Bäckvall, J.-E., Eds.; Tetrahedron Organic Chemistry Series 14; Pergamon: Oxford
    • (c) Gawley, R. E.; Aubé, J. In Principles of Asymmetric Synthesis; Baldwin, J., Williams, R. M., Bäckvall, J.-E., Eds.; Tetrahedron Organic Chemistry Series 14; Pergamon: Oxford, 1996.
    • (1996) Principles of Asymmetric Synthesis
    • Gawley, R.E.1    Aubé, J.2
  • 4
    • 0037124885 scopus 로고    scopus 로고
    • and references therein
    • For Rh-catalyzed isomerization of allylamines, see: (a) Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008 and references therein.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2008
    • Noyori, R.1
  • 28
    • 84957122768 scopus 로고
    • The Z-configuration was confirmed from a medium coupling constant (7.8 Hz) between the olefinic protons. The E-isomer has 13.2 Hz coupling constant. See also: Mueller, K.; Previdoli, F. Helv. Chim. Acta 1981, 64, 2508.
    • (1981) Helv. Chim. Acta , vol.64 , pp. 2508
    • Mueller, K.1    Previdoli, F.2
  • 29
    • 33748508917 scopus 로고    scopus 로고
    • note
    • Pd(II) was found to promote isomerization of 2a into a 55:45 Z/E mixture (THF, room temperature, 72 h).
  • 30
    • 0035823881 scopus 로고    scopus 로고
    • 3 prevents enamine-to-imine isomerization during enamine formation from primary allylamines: Novak, B. M.; Cafmeyer, J. T. J. Am. Chem. Soc. 2001, 123, 11083.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 11083
    • Novak, B.M.1    Cafmeyer, J.T.2
  • 31
    • 33748486804 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details.
  • 32
    • 33748507889 scopus 로고    scopus 로고
    • note
    • A mechanism involving β-hydride elimination is less likely as it is known to proceed with E-selectivity (see ref 2b).
  • 33
    • 33748496114 scopus 로고    scopus 로고
    • note
    • A concerted pathway cannot be ruled out at this point.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.