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Volumn 6, Issue 3, 2004, Pages 325-328

Remarkable Effect of a Silicon Group on the Stereoselectivity of Radical 5-exo-Trig Cyclizations

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; CYCLOPENTANE; RADICAL; SILICON; SULFONE DERIVATIVE;

EID: 1342285530     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036025v     Document Type: Article
Times cited : (19)

References (37)
  • 20
    • 1342338495 scopus 로고    scopus 로고
    • note
    • 2-SePh at -78°C slightly increased the diastereoselectivity, but at the expense of the yield.
  • 21
    • 1342317081 scopus 로고    scopus 로고
    • note
    • 15 and 17 were prepared in 6 and 4 steps from (R)-(-)-citronellene and hexa-1,5-diene, respectively (see Supporting Information).
  • 22
    • 1342274840 scopus 로고    scopus 로고
    • note
    • 2
  • 23
    • 0030007621 scopus 로고    scopus 로고
    • A silicon group may be used as a masked hydroxy group, see: Jones, G. R. ; Landais, Y. Tetrahedron 1996, 52, 7599-7662.
    • (1996) Tetrahedron , vol.52 , pp. 7599-7662
    • Jones, G.R.1    Landais, Y.2
  • 29
    • 1342274842 scopus 로고    scopus 로고
    • note
    • 3 group in the pseudoequatorial position has been preferred over a chairlike conformation with the bulky silicon group in the pseudoaxial position.
  • 30
    • 2742569677 scopus 로고
    • and references therein
    • Lambert, J. B. Tetrahedron 1990, 46, 2677-2689 and references therein.
    • (1990) Tetrahedron , vol.46 , pp. 2677-2689
    • Lambert, J.B.1
  • 31
    • 1342274841 scopus 로고    scopus 로고
    • note
    • C-O bond would be aligned with the incipient C-C bond and thus stabilize more efficiently the developing positive charge at Cl.
  • 32
    • 0001334715 scopus 로고
    • Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, UK
    • (a) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, UK, 1991; Vol. 5, p 1037.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1037
    • Schore, N.E.1
  • 34
    • 1342295993 scopus 로고    scopus 로고
    • note
    • Removal of the sulfonyl group led to a single isomer, indicating that stereochemistry at the ring junction is totally controlled during the Pauson-Khand reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.