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Volumn 118, Issue 16, 1996, Pages 3992-3993

5-endo-trig radical cyclizations: A new means to the stereoselective synthesis of cyclopentanes and diquinanes

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE;

EID: 0029995559     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953806l     Document Type: Article
Times cited : (58)

References (43)
  • 17
    • 15844410066 scopus 로고    scopus 로고
    • 1.5-(π-endo) refers to internal position of olefin during 1,5-H transfer, in contrast to the generally observed 1,5-(π-exo)-H transfer
    • 1.5-(π-endo) refers to internal position of olefin during 1,5-H transfer, in contrast to the generally observed 1,5-(π-exo)-H transfer.
  • 34
    • 0344293778 scopus 로고
    • Thyagarajan, B. S., Ed.; Wiley: New York
    • (a) Singer, L. A. Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1972; Vol. II, pp 239-268.
    • (1972) Selective Organic Transformations , vol.2 , pp. 239-268
    • Singer, L.A.1
  • 36
    • 15844362589 scopus 로고    scopus 로고
    • The ratio of 9a(D)/4a(D) (74%/8%) increases because deuteride is transfered less easily than hydride, and thus, the intramolecular process is favored over the intermolecular one
    • The ratio of 9a(D)/4a(D) (74%/8%) increases because deuteride is transfered less easily than hydride, and thus, the intramolecular process is favored over the intermolecular one.
  • 37
    • 15844394029 scopus 로고    scopus 로고
    • Atomic coordinates for 9b can be obtained on request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 IEZ, UK
    • Atomic coordinates for 9b can be obtained on request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 IEZ, UK.
  • 38
    • 0026504987 scopus 로고
    • Reduction of a vinyl radical bearing a t-Bu group has been observed: Journet, M.; Malacria, M. Tetrahedron Lett. 1992, 33, 1893-1896.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 1893-1896
    • Journet, M.1    Malacria, M.2
  • 39
    • 15844425729 scopus 로고    scopus 로고
    • note
    • Presumably, the steric effects developed by the bulky tert-butyl and isopropyl groups prevents the usual reduction from occurring. The formation of the heterodiquinene 8c (which has been isolated and characterized) could be explained by an initial 5-endo-trig process followed by a rare β-hydrogen atom abstraction. One of the referees suggested an alternative explanation involving an oxidation of the radical 7 to the corresponding cation which then suffers proton loss.
  • 40
    • 0001465664 scopus 로고
    • equation presented
    • The 6-endo-dig cyclization is consistent with the Thorpe-Ingold effect of the bulky diisopropyl group. With a dimethyl group, this process is not observed. See: Magnol, E.; Malacria, M Tetrahedron Lett. 1986, 27, 2255-2256. equation presented
    • (1986) Tetrahedron Lett. , vol.27 , pp. 2255-2256
    • Magnol, E.1    Malacria, M.2
  • 41
    • 15844384392 scopus 로고    scopus 로고
    • A minor quantity of the β-silyl radical incorporated deuterium proving that a 1,5-H transfer is effectively involved in the formation of 6d
    • A minor quantity of the β-silyl radical incorporated deuterium proving that a 1,5-H transfer is effectively involved in the formation of 6d.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.