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Volumn 131, Issue 18, 2009, Pages 6318-6319

Phosphine-promoted [3 + 3] annulations of aziridines with allenoates: Facile entry into highly functionalized tetrahydropyridines

Author keywords

[No Author keywords available]

Indexed keywords

ALLENES; AZIRIDINES; CATALYZED REACTIONS; CYCLOADDITION REACTION; DESULFONYLATION; FUNCTIONALIZED; NUCLEOPHILIC AROMATIC SUBSTITUTION; REACTION PARTNERS; SIMPLE REACTION; TETRAHYDROPYRIDINES;

EID: 69949162395     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8097349     Document Type: Article
Times cited : (190)

References (41)
  • 1
    • 0000629986 scopus 로고
    • database lists 16 books and 1918 reviews on cycloaddition. For a classical review, see: Padwa, A
    • The Chemical Abstracts Service CAS, Trost, B. M, Fleming, I, Eds, Pergamon: New York
    • The Chemical Abstracts Service (CAS) database lists 16 books and 1918 reviews on cycloaddition. For a classical review, see: Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, p 1069.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1069
  • 6
    • 33751156723 scopus 로고    scopus 로고
    • For representative examples of [3 + 2] cycloadditions, see: (a) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906.
    • For representative examples of [3 + 2] cycloadditions, see: (a) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906.
  • 16
    • 70149125231 scopus 로고    scopus 로고
    • The CAS database contains 39 204 references relating to cycloadditions, but only 93 of them relate to [3 + 3] cycloadditions. For reviews on formal [3 + 3] cycloadditions, see: (a) Hsung, R. P.; Kurdyumov, A. V.; Sydorenko, N. Eur. J. Org. Chem. 2005, 23, and references therein.
    • The CAS database contains 39 204 references relating to cycloadditions, but only 93 of them relate to [3 + 3] cycloadditions. For reviews on formal [3 + 3] cycloadditions, see: (a) Hsung, R. P.; Kurdyumov, A. V.; Sydorenko, N. Eur. J. Org. Chem. 2005, 23, and references therein.
  • 23
    • 0042881024 scopus 로고    scopus 로고
    • For recent leading reviews on the synthesis and application of aziridines, see: a
    • For recent leading reviews on the synthesis and application of aziridines, see: (a) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
    • (2003) Chem. Rev , vol.103 , pp. 2905
    • Müller, P.1    Fruit, C.2
  • 28
    • 70149091983 scopus 로고    scopus 로고
    • N-Tosylaziridine was unreactive under the reaction conditions; N-(o-nosyl) aziridine led to a complex mixture of products
    • N-Tosylaziridine was unreactive under the reaction conditions; N-(o-nosyl) aziridine led to a complex mixture of products.
  • 31
    • 70149084581 scopus 로고    scopus 로고
    • The structures of 3aand 3nwere established unequivocally through X-ray crystallographic analyses. See the Supporting Information for details.
    • The structures of 3aand 3nwere established unequivocally through X-ray crystallographic analyses. See the Supporting Information for details.
  • 34
    • 70149115494 scopus 로고    scopus 로고
    • See ref 4g
    • See ref 4g.
  • 35
    • 70149099175 scopus 로고    scopus 로고
    • Employment of an enantiomerically pure aziridine provided an optically pure tetrahydropyridine. See the Supporting Information for details
    • Employment of an enantiomerically pure aziridine provided an optically pure tetrahydropyridine. See the Supporting Information for details.
  • 36
    • 70149121741 scopus 로고    scopus 로고
    • We obtained no crossover product when we reacted the allenaote 2 with a 1:1 mixture of a doubly (deuterium) labeled aziridine and a regular aziridine. See the Supporting Information for details.
    • We obtained no crossover product when we reacted the allenaote 2 with a 1:1 mixture of a doubly (deuterium) labeled aziridine and a regular aziridine. See the Supporting Information for details.
  • 41
    • 70149094142 scopus 로고    scopus 로고
    • We suspect that the deuterium atom on the enamine nitrogen atom is exchanged for a hydrogen atom from the solvent used for NMR spectroscopy; see the Supporting Information for details
    • We suspect that the deuterium atom on the enamine nitrogen atom is exchanged for a hydrogen atom from the solvent used for NMR spectroscopy; see the Supporting Information for details.


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