Mechanistic Aspects of the Boron Trifluoride Catalyzed, Intermolecular Diels-Alder Cycloaddition of an Unactivated 2-Aza 1,3-Diene with Electron-Donating-Substituted Dienophiles

Journal of Organic Chemistry

Volumn 50, Issue 26, 1985, Pages 5678-5686

  Cheng, Yea Shun ^a   Ho, Eugene ^a   Mariano, Patrick S ^a   Ammon, Herman L ^a  

^a UNIVERSITY OF MARYLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845378747     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00350a049     Document Type: Article

References (30)

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17. Preliminary results from current studies in our laboratory have demonstrated that intramolecular analogues of this process occur with high efficiency.
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19. 21 where the yields are generally higher.
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22. 32 proceeds to generate a 1:1 mixture of cycloadducts resulting from competitive endo OR and exo OR transition states
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30. A reviewer has thoughtfully suggested that the lower degree of endo selectivity observed in cycloaddition of 1-morpholinocyclopentene as compared to, for example, that displayed by 1-(trimethylsiloxy)cyclohexene might also reflect the lesser dipole of the C-N vs. C-O bond.