Internally lewis acid-catalyzed diels-alder cycloadditions

Tetrahedron

Volumn 53, Issue 28, 1997, Pages 9637-9646

  Bienaymé, Hugues ^a   Longeau, Alexia ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE;

ARTICLE; CATALYSIS; COVALENT BOND; ENTHALPY; ENTROPY; PRIORITY JOURNAL; STEREOCHEMISTRY;

BETULACEAE;

EID: 0030788404     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00636-4     Document Type: Article

References (56)

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19. A similar effect of regio-and stereocontrol in 1,3 dipolar cycloadditions by internal Lewis acid coordination was recently published: Kanemasa, S.; Tsuruoka, T. Chem. Lett. 1995, 49-50; Kanemasa, S.; Tsuruoka, T.; Yamamoto, H. Tetrahedron Lett. 1995, 36, 5019-5022; Kanemasa, S.; Nishiuchi, M.; Kamimura, A.; Hori, K. J. Am. Chem. Soc. 1994, 116, 2324-2339; Kanemasa, S.; Tsuruoka, T.; Wada, E. Tetrahedron Lett. 1993, 34, 87-90.
20. A similar effect of regio-and stereocontrol in 1,3 dipolar cycloadditions by internal Lewis acid coordination was recently published: Kanemasa, S.; Tsuruoka, T. Chem. Lett. 1995, 49-50; Kanemasa, S.; Tsuruoka, T.; Yamamoto, H. Tetrahedron Lett. 1995, 36, 5019-5022; Kanemasa, S.; Nishiuchi, M.; Kamimura, A.; Hori, K. J. Am. Chem. Soc. 1994, 116, 2324-2339; Kanemasa, S.; Tsuruoka, T.; Wada, E. Tetrahedron Lett. 1993, 34, 87-90.
21. A similar effect of regio-and stereocontrol in 1,3 dipolar cycloadditions by internal Lewis acid coordination was recently published: Kanemasa, S.; Tsuruoka, T. Chem. Lett. 1995, 49-50; Kanemasa, S.; Tsuruoka, T.; Yamamoto, H. Tetrahedron Lett. 1995, 36, 5019-5022; Kanemasa, S.; Nishiuchi, M.; Kamimura, A.; Hori, K. J. Am. Chem. Soc. 1994, 116, 2324-2339; Kanemasa, S.; Tsuruoka, T.; Wada, E. Tetrahedron Lett. 1993, 34, 87-90.
22. A similar effect of regio-and stereocontrol in 1,3 dipolar cycloadditions by internal Lewis acid coordination was recently published: Kanemasa, S.; Tsuruoka, T. Chem. Lett. 1995, 49-50; Kanemasa, S.; Tsuruoka, T.; Yamamoto, H. Tetrahedron Lett. 1995, 36, 5019-5022; Kanemasa, S.; Nishiuchi, M.; Kamimura, A.; Hori, K. J. Am. Chem. Soc. 1994, 116, 2324-2339; Kanemasa, S.; Tsuruoka, T.; Wada, E. Tetrahedron Lett. 1993, 34, 87-90.
23. Will be published separately.
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29. Such tandem reaction sequences are known to give γ-substitution products: Ballester, P.; Costa, A.; Raso, A.G.; Gomez-Solivellas, A.; Mestres, R. J. Chem. Soc. Perkin Trans. I 1988, 1711-1717; Ballester, P.; Garcia-Raso, A.; Gomez-Solivellas, A.; Mestres, R. Tetrahedron Lett. 1985, 26, 2485-2488.
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49. For a stepwise mechanism, rapid rotation around the C5-C6 bond in the Michael addition intermediate would yield a mixture of cis/trans products, irrespective of the dienophile stereochemistry.
50. Prepared from 1-trimethylsiloxy-1,3-cyclohexadiene: Clarke, C.; Fleming, I.; Fortunak, J.D.M.; Gallagher, P.T. Tetrahedron 1988, 44, 3931-3944.
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53. 1-Trimethylsiloxy-1,3,5-hexatriene is a mixture of E,E,E (roughly 75%) and Z,E,E isomers. Traces of other stereoisomers are also present. A slight excess was used (1.5 equiv.).
54. Both acidic (protic) and ketone/aldehyde-containing dienophiles did not give the cycloaddition reaction with diene 13, setting the major limitations of this methodology.
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