Syntheses of Highly Functionalized Spirocyclohexenes by Formal [4+2] Annulation of Arylidene Azlactones with Allenoates
(2018) Asian Journal of Organic Chemistry — Vol. 7, n° 8, p. 1620-1625 (2018)
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- Authors
Waser, Mario 
- 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.
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Citations
Eitzinger, A., Zielke, K., Widhalm, M., Robiette, R., & Waser, M. (2018). Syntheses of Highly Functionalized Spirocyclohexenes by Formal [4+2] Annulation of Arylidene Azlactones with Allenoates. Asian Journal of Organic Chemistry, 7(8), 1620-1625. https://doi.org/10.1002/ajoc.201800275 (Original work published 2018)