메뉴 건너뛰기




Volumn 12, Issue 18, 2010, Pages 3968-3971

Formal nucleophilic substitution of bromocyclopropanes with amides en route to conformationally constrained β-amino acid derivatives

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINO ACID; BROMINE DERIVATIVE; CYCLOPROPANE DERIVATIVE;

EID: 77956602331     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101228k     Document Type: Article
Times cited : (42)

References (53)
  • 1
    • 77956607072 scopus 로고    scopus 로고
    • See, for example
    • See, for example
  • 4
    • 77956598449 scopus 로고    scopus 로고
    • For leading reviews, see
    • For leading reviews, see
  • 7
    • 77956595629 scopus 로고    scopus 로고
    • See, for recent examples
    • See, for recent examples
  • 12
    • 77956605014 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 14
    • 17944396657 scopus 로고    scopus 로고
    • Chemistry and Biology of β-Amino Acids
    • Hoekstra, W. J. Chemistry and Biology of β-Amino Acids Curr. Med. Chem. 1999, 6, 905
    • (1999) Curr. Med. Chem. , vol.6 , pp. 905
    • Hoekstra, W.J.1
  • 22
    • 77956599071 scopus 로고    scopus 로고
    • For our recent reports on preparative synthesis of isolable cyclopropenes, see
    • For our recent reports on preparative synthesis of isolable cyclopropenes, see
  • 25
    • 77956566695 scopus 로고    scopus 로고
    • For discussion, see
    • For discussion, see
  • 30
    • 77956575115 scopus 로고    scopus 로고
    • See for example
    • See for example
  • 36
    • 77956589083 scopus 로고    scopus 로고
    • For ring-retentive nucleophilic addition of amines to cyclopropenes, see
    • For ring-retentive nucleophilic addition of amines to cyclopropenes, see
  • 38
    • 0001263290 scopus 로고
    • For nucleophilic displacement of halogen in cyclopropyl halides with N -heterocycles, amides, and sulfamides, see:
    • Franck-Neumann, M.; Miesch, M.; Kempf, H. Tetrahedron 1988, 44, 2933 For nucleophilic displacement of halogen in cyclopropyl halides with N -heterocycles, amides, and sulfamides, see:
    • (1988) Tetrahedron , vol.44 , pp. 2933
    • Franck-Neumann, M.1    Miesch, M.2    Kempf, H.3
  • 42
    • 77956567723 scopus 로고    scopus 로고
    • For ring retentive installation of phosphorous-based nucleophilic moiety into pre-existing three-membered cycle, see
    • For ring retentive installation of phosphorous-based nucleophilic moiety into pre-existing three-membered cycle, see
  • 50
    • 77956579285 scopus 로고    scopus 로고
    • It is believed that a fine balance between acidity and nucleofilicity of the pronucleophile is essential for the successful transformation. See ref 9 for discussion.
    • It is believed that a fine balance between acidity and nucleofilicity of the pronucleophile is essential for the successful transformation. See ref 9 for discussion.
  • 51
    • 77956563016 scopus 로고    scopus 로고
    • We have also previously demonstrated a single example of a formal nucleophilic substitution of 1a with pyrrole. Studies on incorporation of other heterocyclic moieties in the three-membered ring via this approach are currently underway and will be reported in due course
    • We have also previously demonstrated a single example of a formal nucleophilic substitution of 1a with pyrrole. Studies on incorporation of other heterocyclic moieties in the three-membered ring via this approach are currently underway and will be reported in due course.
  • 52
    • 77956589504 scopus 로고    scopus 로고
    • Although never observed directly, intermediate i was proved in the reaction of 5a with phenoxides. See ref 9
    • Although never observed directly, intermediate i was proved in the reaction of 5a with phenoxides. See ref 9.
  • 53
    • 77956561984 scopus 로고    scopus 로고
    • We failed to detect any cyclopropane-containing products in this reaction
    • We failed to detect any cyclopropane-containing products in this reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.