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Volumn 63, Issue 20, 1998, Pages 6772-6773

Symmetry breaking of novel C2 chiral across-ring 1,3-dienes

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Indexed keywords


EID: 0011168457     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981296i     Document Type: Article
Times cited : (3)

References (47)
  • 5
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    • John Wiley and Sons: New York
    • As chiral templates, see: (e) Ho, T.-L. Tactics of Organic Synthesis; John Wiley and Sons: New York, 1994; pp 348-373.
    • Tactics of Organic Synthesis , vol.1994 , pp. 348-373
    • Ho, T.-L.1
  • 8
    • 33646817626 scopus 로고
    • Enzymatically controlled symmetry-breaking steps are part of key biological processes, i.e., biosynthesis of triterpenes from squalene.
    • (b) Bertz, S. H.; Sommer, T. J. In Organic Synthesis. Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; pp 83-87. Enzymatically controlled symmetry-breaking steps are part of key biological processes, i.e., biosynthesis of triterpenes from squalene.
    • (1993) Organic Synthesis. Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT , vol.83
    • Bertz, S.H.1    In, S.T.J.2
  • 12
    • 33847086269 scopus 로고
    • Chiral 1,3-dienes have attracted an increased attention from the pioneering work of Trost. They remain unusual compounds. For leading references, see: (a) Trost, B. M.; O'Krongly, D. J.; Belletire, L. J. Am. Chem. Soc. 1980,102,7595-7596.
    • (1980) J. Am. Chem. Soc. , pp. 7595-7596
    • Trost, B.M.1    O'Krongly, D.J.2    Belletire, L.3
  • 25
    • 0000458209 scopus 로고
    • For a review on substrate-directible reactions including allylic alcohols, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
    • (1993) Chem. Rev. , vol.93 , pp. 1307-1370
    • Hoveyda, A.H.1    Evans, D.A.2    Fu, G.C.3
  • 29
    • 0001640928 scopus 로고    scopus 로고
    • For a review on the Mitsunobu reaction, see: Hughes, D. L. Org. Prep. Proc. Int. 1996,28, 127-164.
    • (1996) Org. Prep. Proc. Int. , vol.28 , pp. 127-164
    • Hughes, D.L.1
  • 32
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    • In our hands, the preparation of diene 3 by the procedure of Piers was unsuccessful.
    • (b) Beddoes, R. L.; Cheeseright, T.; Wang, J.; Quayle, P. Tetrahedron Lett. 1995,36,283-286. In our hands, the preparation of diene 3 by the procedure of Piers was unsuccessful.
    • (1995) Tetrahedron Lett. , vol.36
    • Beddoes, R.L.1    Cheeseright, T.2    Wang, J.3    Quayle, P.4
  • 34
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    • note
    • 2 is used.
  • 35
    • 33646764075 scopus 로고    scopus 로고
    • note
    • (a) meso-3 and rac-3 can be readily separated by taking advantage of the fact that they are solid and liquid, respectively, at 0 °C. For a study on the conformational equilibrium of dienes meso-3 and rac-3, see:
  • 39
    • 33646774166 scopus 로고
    • For a discussion about the importance of degenerate operations in organic synthesis, see
    • (a) Ono, N.; Karnimura, A.; Kaji, A. J. Org. Chem. 1986,57, 21392142. For a discussion about the importance of degenerate operations in organic synthesis, see:
    • (1986) J. Org. Chem. , vol.57 , pp. 21392142
    • Ono, N.1    Karnimura, A.2    Kaji, A.3
  • 43
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    • Deduced from NMR data and MM3* calculations; see the Supporting Information.
    • Deduced from NMR data and MM3* calculations; see the Supporting Information.
  • 47
    • 85087246150 scopus 로고    scopus 로고
    • 13CNMR, MS, IR, optical rotations, and elemental analysis) were obtained for all new compounds. The structure of compounds 10-18 was established by NOESY and J coupling analysis.
    • 13CNMR, MS, IR, optical rotations, and elemental analysis) were obtained for all new compounds. The structure of compounds 10-18 was established by NOESY and J coupling analysis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.