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Volumn 28, Issue 22, 1987, Pages 2447-2450

Effect of dienophile activating group on the stereoselectivity of the intramolecular diels-alder reaction

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EID: 0000094509     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)95437-6     Document Type: Article
Times cited : (31)

References (20)
  • 13
    • 84918452184 scopus 로고    scopus 로고
    • 3) δ 5.96 (br d, J = 10.0 Hz, 1H), 5.55 (br d, J = 10.0 Hz, 1H), 3.45 (m, 4H), 2.70 (dd, J = 10.1, 8.0Hz, 1H), 2.50 (br s, 1H), 2.02–1.59 (m, 12H), 1.18 (m, 1H), 0.93 (d, J = 6.9 Hz, 3H), 0.88 (d, J = 6.7 Hz, 3H). Data for 7a: mp 61–62°C; NMR (250 MHz) δ 5.82 (dt, J = 10.1, 3.3 Hz, 1H), 5.54 (br d, J = 10.1 Hz, 1H), 3.48 (m, 4H), 2.42 (m, 3H), 2.27 (dd, J = 10.7, 10.5 Hz, 1H), 1.95–1.55 (m, 10H), 1.29 (m, 1H), 0.95 (d, J = 6.8 Hz, 3H), 0.74 (d, J = 6.8 Hz, 3H). Data for 6c: mp 41–42°C; NMR (250 MHz) δ 5.98 (br d, J = 10.0 Hz, 1H), 5.58 (dt, J = 10.0, 3.0 Hz, 1H), 2.78 (dd, J = 10.5, 7.6 Hz, 1H), 2.71 (m, 1H), 2.14 (s, 3H), 1.98 (m, 1H), 1.80–1.52 (m, 7H), 1.17 (m, 1H), 0.96 (d, J = 6.8 Hz, 3H), 0.77 (d, J = 6.3 Hz, 3H). Partial data for 7c, not separable from 6c, : NMR δ 5.84 (br d), 0.75 (d). Data for [[Truncated]]
  • 14
    • 1542792683 scopus 로고
    • For previous studies of intramolecular Diels-Alder reactions of terminally activated triene aldehydes, see
    • (1986) J. Org. Chem. , vol.51 , pp. 1633
    • Marshall1    Grote2    Shearer3
  • 20
    • 84918452183 scopus 로고    scopus 로고
    • The limited amount of data currently available leads us to suspect that endo stabilizing effects will dominate the “twist asynchronous” mode of cyclization with highly activated (Z)-1,7,9-decatrienes (see ref. 6b for the lewis acid catalyzed cyclization of, Z)-5a).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.