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Volumn 44, Issue 34, 2005, Pages 5523-5526

Asymmetric photocycloaddition in solution of a chiral crystallized naphthamide

Author keywords

Asymmetric synthesis; Chirality; Cycloaddition; Enantioselectivity; Photochemistry

Indexed keywords

ADDITION REACTIONS; CONFORMATIONS; CRYSTALLIZATION; CRYSTALS; PHOTOCHEMICAL REACTIONS; SYNTHESIS (CHEMICAL);

EID: 24644506219     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501156     Document Type: Article
Times cited : (49)

References (34)
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    • b) S. F. Mason, Nature 1984, 311, 19-23;
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    • Mason, S.F.1
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    • A few examples involving solid-gas reactions were reported, however, the enantioselectivity is low. See: a) K. Penzein, G. M. J. Schmidt, Angew. Chem. 1969, 81, 628;
    • (1969) Angew. Chem. , vol.81 , pp. 628
    • Penzein, K.1    Schmidt, G.M.J.2
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    • note
    • 2 = 0.2369, and GOF = 1.149 for 2903 reflections.
  • 26
    • 0001597354 scopus 로고
    • For a report on the photochemical cycloaddition of anthracene and 1-cyanonaphthalene, see: A. Albini, E. Fasani, D. Faiardi, J. Org. Chem. 1987, 52, 155-157.
    • (1987) J. Org. Chem. , vol.52 , pp. 155-157
    • Albini, A.1    Fasani, E.2    Faiardi, D.3
  • 28
    • 24644518793 scopus 로고    scopus 로고
    • 2 = 0.2242, and GOF = 1.149 for 2903 reflections. CCDC 207437 (1a), 267438 (1b), and 267439 (2a) contain the supplementary crystallographic data for this paper These data can he obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
  • 30
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    • Angew. Chem. Int. Ed. 2003, 42, 4360-4363;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 4360-4363
  • 34
    • 24644451424 scopus 로고    scopus 로고
    • note
    • Seeding was carried out as follows: the melted sample of 1a at 120°C was gradually cooled, and a powdered single crystal (about 0.5 mm size) was added at below the melting point of 110-112°C. The presence of the seed crystal induces the same conformation in the subsequent crystallization such that all the crystals in the batch have the same optical rotation.


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