Heterocyclic synthesis via the tandem thionium/n-acylinnnium ion cascade

Journal of Organic Chemistry

Volumn 63, Issue 20, 1998, Pages 6778-6779

  Padwa, Albert ^a   Heidelbaugh, Todd M ^a   Kuethe, Jeffrey T ^a   McClure, Michael S ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000085486     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981349w     Document Type: Article

References (19)

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19. One explanation to rationalize formation of a single diastereomer from the DMTSF-induced cyclization would involve facile equilibration of the carbomethoxy-bearing stereogenic center via tautomerization of the JV-acyliminium ion intermediate prior to the final ring closure. Alternatively, the direction of conrotatory closure may be influenced by the presence of the neighboring carbomethoxy group. Further work is in progress to clarify this issue and unequivocally established the stereochemistry of the cyclized products.