Syntheses of Highly Functionalized Spirocyclohexenes by Formal (4+2) Annulation of Arylidene Azlactones with Allenoates

Abstract: A straightforward phosphine‐catalyzed formal [4+2] annulation between α‐branched allenoates and arylidene azlactones has been developed to access highly functionalized spirocyclohexenes. This cyclization favors the γ‐addition of the phosphine‐activated allenoates over a β′‐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.

Location
Deutsche Nationalbibliothek Frankfurt am Main
Extent
Online-Ressource
Language
Englisch

Bibliographic citation
Syntheses of Highly Functionalized Spirocyclohexenes by Formal (4+2) Annulation of Arylidene Azlactones with Allenoates ; volume:7 ; number:8 ; year:2018 ; pages:1620-1625 ; extent:6
Asian journal of organic chemistry ; 7, Heft 8 (2018), 1620-1625 (gesamt 6)

Creator
Eitzinger, Andreas
Zielke, Katharina
Widhalm, Michael
Robiette, Raphaël
Waser, Mario

DOI
10.1002/ajoc.201800275
URN
urn:nbn:de:101:1-2022091006542621265898
Rights
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Last update
15.08.2025, 7:33 AM CEST

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Associated

  • Eitzinger, Andreas
  • Zielke, Katharina
  • Widhalm, Michael
  • Robiette, Raphaël
  • Waser, Mario

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