메뉴 건너뛰기




Volumn 46, Issue 6, 2007, Pages 937-940

Chiral dendralenes for rapid access to enantiomerically pure polycycles

Author keywords

Cross coupling; Cycloaddition; Dendralenes; Domino reactions; Fused ring systems

Indexed keywords

ATOMS; POLYCYCLIC AROMATIC HYDROCARBONS; SELF ASSEMBLY; STEREOCHEMISTRY;

EID: 33846686864     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603335     Document Type: Article
Times cited : (52)

References (50)
  • 1
    • 24644517245 scopus 로고    scopus 로고
    • Eds, H.-G. Schmalz, T. Wirth, Wiley-VCH, Weinheim
    • H. Hopf in Organic Synthesis Highlights V (Eds.: H.-G. Schmalz, T. Wirth), Wiley-VCH, Weinheim, 2003, pp. 419-427.
    • (2003) Organic Synthesis Highlights V , pp. 419-427
    • Hopf, H.1
  • 3
    • 0001105257 scopus 로고    scopus 로고
    • H. Hopf, Angew. Chem. 2001, 113, 727-729;
    • (2001) Angew. Chem , vol.113 , pp. 727-729
    • Hopf, H.1
  • 4
    • 0035804403 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 705-707.
    • (2001) Chem. Int. Ed , vol.40 , pp. 705-707
    • Angew1
  • 5
    • 0000592651 scopus 로고
    • H. Hopf, Angew. Chem. 1984, 96, 947-958;
    • (1984) Angew. Chem , vol.96 , pp. 947-958
    • Hopf, H.1
  • 8
    • 0001202346 scopus 로고    scopus 로고
    • W. J. Bailey, J. Economy, J. Am. Chem. Soc. 1955, 77, 1133-1136;
    • b) W. J. Bailey, J. Economy, J. Am. Chem. Soc. 1955, 77, 1133-1136;
  • 29
    • 33846662394 scopus 로고    scopus 로고
    • Ingenious stereoselective sequences involving a decatrienone-type intramolecular cycloaddition followed by an intermolecular cycloaddition have been reported by Fallis and co-workers; see Refs[6j]and[6q
    • Ingenious stereoselective sequences involving a decatrienone-type intramolecular cycloaddition followed by an intermolecular cycloaddition have been reported by Fallis and co-workers; see Refs[6j]and[6q].
  • 30
    • 0000479137 scopus 로고    scopus 로고
    • For a review of sequences of Diels-Alder reactions, see
    • For a review of sequences of Diels-Alder reactions, see: J. D. Winkler, Chem. Rev. 1996, 96, 167-176.
    • (1996) Chem. Rev , vol.96 , pp. 167-176
    • Winkler, J.D.1
  • 36
    • 0032532537 scopus 로고    scopus 로고
    • For highly Z-selective Stille monocouplings of 1,1-dibromoalkenes with organostannanes, see: L. Wang, W. Shen, Tetrahedron Lett. 1998, 39, 7625-7628.
    • For highly Z-selective Stille monocouplings of 1,1-dibromoalkenes with organostannanes, see: L. Wang, W. Shen, Tetrahedron Lett. 1998, 39, 7625-7628.
  • 40
    • 33846705907 scopus 로고    scopus 로고
    • As expected, all the cycloadditions of maleic anhydride and benzoquinones reported here were found to proceed exclusively through the endo mode.
    • As expected, all the cycloadditions of maleic anhydride and benzoquinones reported here were found to proceed exclusively through the endo mode.
  • 41
    • 33846684625 scopus 로고    scopus 로고
    • Small amounts of products resulting from the trans-fused isomer of 9 are also witnessed. The trans isomer of 9 is formed through an intramolecular Diels-Alder reaction.[14]
    • Small amounts of products resulting from the trans-fused isomer of 9 are also witnessed. The trans isomer of 9 is formed through an intramolecular Diels-Alder reaction.[14]
  • 42
    • 33846664542 scopus 로고    scopus 로고
    • Computational investigations into the origins of the stereoselectivity in these reactions are under way, and the results of these investigations will be reported shortly
    • Computational investigations into the origins of the stereoselectivity in these reactions are under way, and the results of these investigations will be reported shortly.
  • 43
    • 33846659769 scopus 로고    scopus 로고
    • Precipitation of the monoadduct from solution is not necessary for the synthesis of the compounds depicted in Scheme 4; this method is preferred, however, since it leads to the clean formation of mixed double and quadruple cycloadducts
    • Precipitation of the monoadduct from solution is not necessary for the synthesis of the compounds depicted in Scheme 4; this method is preferred, however, since it leads to the clean formation of "mixed" double and quadruple cycloadducts.
  • 44
    • 0242490677 scopus 로고    scopus 로고
    • Clean inversion of configuration has been seen in the coupling of organozinc compounds with 2-bromo-1,3-butadienes, see: X. Zeng, Q. Hu, M. Qian, E.-i. Negishi, J. Am. Chem. Soc. 2003, 125, 13636-13637. The stereochemistry of geometrical isomers 25 and 28 was confirmed by NOESY experiments (see the Supporting Information).
    • Clean inversion of configuration has been seen in the coupling of organozinc compounds with 2-bromo-1,3-butadienes, see: X. Zeng, Q. Hu, M. Qian, E.-i. Negishi, J. Am. Chem. Soc. 2003, 125, 13636-13637. The stereochemistry of geometrical isomers 25 and 28 was confirmed by NOESY experiments (see the Supporting Information).
  • 45
    • 0001016532 scopus 로고    scopus 로고
    • For the use of 3-(tributylstannyl)-3-sulfolene for the synthesis of unsubstituted dendralenes
    • For the use of 3-(tributylstannyl)-3-sulfolene for the synthesis of unsubstituted dendralenes: S. Fielder, D. D. Rowan, M. S. Sherburn, Angew. Chem. 2000, 112, 4501-4503;
    • (2000) Angew. Chem , vol.112 , pp. 4501-4503
    • Fielder, S.1    Rowan, D.D.2    Sherburn, M.S.3
  • 46
    • 0034605940 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 4331-4333.
    • (2000) Chem. Int. Ed , vol.39 , pp. 4331-4333
    • Angew1
  • 47
    • 33846672155 scopus 로고    scopus 로고
    • Thermal ellipsoid plots are included in the Supporting Information. CCDC-609 960-609964 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
    • Thermal ellipsoid plots are included in the Supporting Information. CCDC-609 960-609964 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.