메뉴 건너뛰기




Volumn 62, Issue 45, 2006, Pages 10541-10554

The allenic Alder-ene reaction: constitutional group selectivity and its application to the synthesis of ovalicin

Author keywords

Alder ene; Allenes; Catalysis; Iridium; Rhodium; Trienes

Indexed keywords

ALLENE DERIVATIVE; ANGIOGENESIS INHIBITOR; IRIDIUM; OVALICIN; RUTHENIUM; SOLVENT; UNCLASSIFIED DRUG;

EID: 33748963246     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.06.115     Document Type: Article
Times cited : (18)

References (67)
  • 2
    • 33748986430 scopus 로고    scopus 로고
    • For a review on the Alder-ene reaction, see:
  • 3
    • 0001899585 scopus 로고
    • Ene Reactions with Alkenes as Enophiles
    • Trost B.M. (Ed), Pergamon, Oxford, England
    • Snider B.B. Ene Reactions with Alkenes as Enophiles. In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon, Oxford, England 1-27
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1-27
    • Snider, B.B.1
  • 4
    • 84906438197 scopus 로고    scopus 로고
    • Brummond, K. M.; Loyer-Drew, J. A. C-C Bond Formation (Part 1) by Addition Reactions: Alder-ene Reaction. In Comprehensive Organometallic Chemistry III; Crabtree, R. H., Mingos, M. P., Ojima, I., Eds.; Elsevier: Oxford; Vol. 10, Chapter 10.03.06, in press.
  • 14
    • 84890671103 scopus 로고    scopus 로고
    • The Rhodium(I)-Catalyzed Alder-Ene Reaction
    • Evans P.A. (Ed), Wiley-VCH, Weinheim
    • Brummond K.M., and McCabe J.M. The Rhodium(I)-Catalyzed Alder-Ene Reaction. In: Evans P.A. (Ed). Modern Rhodium-Catalyzed Organic Reactions (2005), Wiley-VCH, Weinheim 151-172
    • (2005) Modern Rhodium-Catalyzed Organic Reactions , pp. 151-172
    • Brummond, K.M.1    McCabe, J.M.2
  • 18
    • 33748983636 scopus 로고    scopus 로고
    • note
    • In Malacria's case a tert-butyl group on the proximal double bond of the allene was essential for reaction to occur at the distal double bond. Likewise, Sato's substrate required a short two carbon tether on the allenyne in order for the reaction to occur at the distal double bond of the allene.
  • 19
    • 0037198748 scopus 로고    scopus 로고
    • Computational insight concerning catalytic decision points of the transition metal-catalyzed [2+2+1] cycloisomerization reaction of allenes.
    • Brummond K.M., Chen H., Fisher K.D., Kerekes A.D., Rickards B., Sill P.C., and Geib S.J. Org. Lett. 4 (2002) 1931 Computational insight concerning catalytic decision points of the transition metal-catalyzed [2+2+1] cycloisomerization reaction of allenes.
    • (2002) Org. Lett. , vol.4 , pp. 1931
    • Brummond, K.M.1    Chen, H.2    Fisher, K.D.3    Kerekes, A.D.4    Rickards, B.5    Sill, P.C.6    Geib, S.J.7
  • 20
    • 33748959413 scopus 로고    scopus 로고
    • Bayden, A. S.; Brummond, K. M.; Jordan, K. D., submitted for publication.
  • 51
    • 33748975063 scopus 로고    scopus 로고
    • note
    • Addition of benzenesulfinic acid sodium salt to 5-chloro-1-(trimethylsilyl)-1-pentyne gave 26% yield of 14 contaminated with O-alkylated by-product.
  • 54
    • 33748960132 scopus 로고    scopus 로고
    • see Brummond and Loyer-Drew in Ref. 2.
  • 55
    • 33748957243 scopus 로고    scopus 로고
    • note
    • The first step was problematic due to the instability of the ethyl glyoxylate and its ease of polymerization.
  • 58
    • 0025931968 scopus 로고
    • 4CuLi gave a 2:1 ratio of 22a:23 and is believed to result from a two electron transfer process. See:
    • 4CuLi gave a 2:1 ratio of 22a:23 and is believed to result from a two electron transfer process. See:. Krause N., and Handke G. Tetrahedron Lett. 32 (1991) 7229
    • (1991) Tetrahedron Lett. , vol.32 , pp. 7229
    • Krause, N.1    Handke, G.2
  • 59
    • 0002051108 scopus 로고
    • Enyne 23 was characterized after didesilylation using TBAF
    • House H.O. Acc. Chem. Res. 9 (1976) 59 Enyne 23 was characterized after didesilylation using TBAF
    • (1976) Acc. Chem. Res. , vol.9 , pp. 59
    • House, H.O.1
  • 60
    • 33748983107 scopus 로고    scopus 로고
    • note
    • Characterization of the geometric isomers (E-24a, Z-24a) was obtained by ROESY NMR experiments on the desilylated primary hydroxyl group.
  • 63
    • 33748973092 scopus 로고    scopus 로고
    • note
    • This hypothesis is supported by the strongest coordinating hydroxyl group yielding the most constitutional isomer 25. Coordination effects have been suggested by Trost's Pd-catalyzed cycloisomerizations where olefins coordinated to the Pd-metallocycle giving enhanced regioselectivities.
  • 64
    • 33748975970 scopus 로고    scopus 로고
    • note
    • 1H NMR of trienes E-17a, Z-17a, and 18a the olefinic peaks are almost identical in chemical shift, and, as expected, the ratio of products was the same.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.