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Volumn 7, Issue 15, 2005, Pages 3379-3381

Cycloisomerization of dienes with carbophilic Lewis acids: Mimicking terpene biosynthesis with Pt(II) catalysts

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; PLATINUM; TERPENE; THUJANE;

EID: 23044437977     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051277c     Document Type: Article
Times cited : (47)

References (48)
  • 4
  • 28
    • 23044436587 scopus 로고    scopus 로고
    • note
    • The balance of material in these reactions is usually alkene-containing isomers that appear to originate from the consumption of cyclopropane.
  • 29
    • 23044495830 scopus 로고    scopus 로고
    • note
    • 31P NMR.
  • 30
    • 23044443003 scopus 로고    scopus 로고
    • note
    • This nomenclature refers to the position of the electrophilic alkene in the C-C bond-forming transition state.
  • 31
    • 4444225192 scopus 로고    scopus 로고
    • Both 6-exo- and 6-endocyclization modes were observed in stoichiometric cascade cyclization of polyenes. See: Koh, J. H.; Gagné, M. R. Angew. Chem., Int. Ed. 2004, 43, 3459-3461.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3459-3461
    • Koh, J.H.1    Gagné, M.R.2
  • 34
    • 23044470655 scopus 로고    scopus 로고
    • note
    • The balance of the material was two Pt-alkyls that remain uncharacterized.
  • 36
    • 23044465993 scopus 로고    scopus 로고
    • note
    • A single diastereomer was obtained from reductive cleavage of 13b. Although trans relative stereochemistry seems most likely, this has not been conclusively determined.
  • 37
    • 23044467458 scopus 로고    scopus 로고
    • note
    • A similar OBn abstraction likely mediates the isomerization of 10 to O-Bn geraniol/nerol (entry 5, Table 1).
  • 38
    • 23044509849 scopus 로고    scopus 로고
    • note
    • +.
  • 48
    • 23044458378 scopus 로고    scopus 로고
    • see ref 2b
    • An alternative possibility is direct metalation to form a Pt(IV) metallacyclobutane followed by reductive elimination. Evidence disfavoring this mechanism includes the observation of cyclopropane products with related Pd(II) catalysts, which would implicate the involvement of a Pd(IV) intermediate; see ref 2b. However, this possibility has not been rigorously disproven.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.