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Title
Syntheses of Highly Functionalized Spirocyclohexenes by Formal [4+2] Annulation of Arylidene Azlactones with Allenoates
AuthorEitzinger, Andreas ; Zielke, Katharina ; Widhalm, Michael ; Robiette, Raphael ; Waser, Mario
Published in
Asian Journal of Organic Chemistry, 2018, Vol. 7, Issue 8, page 1620-1625
PublishedWiley, 2018
LanguageEnglish
Document typeJournal Article
ISSN2193-5815
URNurn:nbn:at:at-ubl:3-628 Persistent Identifier (URN)
DOI10.1002/ajoc.201800275 
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Syntheses of Highly Functionalized Spirocyclohexenes by Formal [4+2] Annulation of Arylidene Azlactones with Allenoates [1.07 mb]
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Abstract (English)

A straightforward phosphinecatalyzed formal [4+2] annulation between branched allenoates and arylidene azlactones has been developed to access highly functionalized spirocyclohexenes. This cyclization favors the addition of the phosphineactivated allenoates over a ′addition pathway. Detailed computational studies support the proposed mechanism and provide a reasonable explanation for the observed regioselectivity and the noted effect of the catalyst.

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