Syntheses of Highly Functionalized Spirocyclohexenes by Formal [4+2] Annulation of Arylidene Azlactones with Allenoates.

Asian Journal of Organic Chemistry
Andreas EitzingerMario Waser

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

Apr 26, 2019·Chemistry : a European Journal·Katharina ZielkeMario Waser

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Methods Mentioned

BETA
NMR
X‐ray
column chromatography

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