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Volumn 127, Issue 15, 2005, Pages 5518-5527

Stereochemistry of hexenyl radical cyclizations with tert-butyl and related large groups: Substituent and temperature effects

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYSIS; CHEMICAL BONDS; HYDROGENATION; THERMAL EFFECTS; X RAY ANALYSIS;

EID: 17644427636     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042595u     Document Type: Article
Times cited : (49)

References (38)
  • 4
    • 0001216647 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K.
    • (d) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 4, pp 715-831.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 715-831
    • Curran, D.P.1
  • 5
    • 0000599639 scopus 로고
    • Tanner, D. D., Ed.; JAI: Greewich, CT
    • Curran, D. P. In Advances in Free Radical Chemisty; Tanner, D. D., Ed.; JAI: Greewich, CT, 1990; Vol. 1, pp 121-157.
    • (1990) Advances in Free Radical Chemisty , vol.1 , pp. 121-157
    • Curran, D.P.1
  • 23
    • 85214770572 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany
    • Yorimitsu, H.; Oshima, K. In Radicals in Organic Synthesis, 1st ed.; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, pp 11-27.
    • (2001) Radicals in Organic Synthesis, 1st Ed. , vol.1 , pp. 11-27
    • Yorimitsu, H.1    Oshima, K.2
  • 25
    • 17644389626 scopus 로고    scopus 로고
    • note
    • After structural correction, the relative chemical shifts of the methyl and ten-butyl resonances exhibit the same trends for 19 and 28: 28-cis, 0.93 (s 9 H), 0.85 (d, 3 H, J = 7.1 Hz); 28-trans 0.97 (d, 3 H, J = 6.8 Hz), 0.84 (s, 9 H); 19-cis, 0.96 (s, 9 H), 0.91 (d, 3 H); 19-trans, 1.00 (d, 3 H, J = 7 HZ), 0.88 (s, 9 H). In the eis isomer, the methyl doublet resonates upfield from the tert-butyl singlet, while in the trans isomer the positions of these resonances are reversed.
  • 27
    • 17644384556 scopus 로고    scopus 로고
    • note
    • One minor product peak from this experiment did not match the GC peak for the very minor product 37 formed in the reduction of 18. This suggests either that the structure of 37 might be wrong or that 10a and 11a might be isomers at the ester bearing carbon rather than the ring fusion. Since the structures of all these minor product are tentative and since 37 was only formed in trace amounts, we decided not to pursue this issue further.
  • 33
    • 17644416468 scopus 로고    scopus 로고
    • note
    • The alcohol shown below is formed by hydroboration of 40, and the stereoselectivity of the hydroboration (addition trans to the tert-butyl group) suggests that the Beckwith assumption of (kinetic) addition of hydrogen trans to the tert-butyl group is reasonable. To confirm the configuration of this alcohol, we converted it to the thionocarbonate followed by Barton-McCombie deoxygentation. This gave 28-cis as the only product. Further, the crystal structure of the derived 3,5-dinitrobezoate ester was also solved. See the Supporting Information for details. (Chemical Equation Presented)
  • 34
    • 0000617227 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K.
    • Siegel, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 8, pp 417-442.
    • (1991) Comprehensive Organic Synthesis , vol.8 , pp. 417-442
    • Siegel, S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.