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- Title
Syntheses of Highly Functionalized Spirocyclohexenes by Formal [4+2] Annulation of Arylidene Azlactones with Allenoates.
- Authors
Eitzinger, Andreas; Zielke, Katharina; Widhalm, Michael; Robiette, Raphaël; Waser, Mario
- Abstract
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.
- Subjects
CYCLOHEXANE derivatives; RING formation (Chemistry); ANNULATION; PHOSPHINE; REGIOSELECTIVITY (Chemistry)
- Publication
Asian Journal of Organic Chemistry, 2018, Vol 7, Issue 8, p1620
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.201800275