Cyclization cascades initiated by 1,6-conjugate addition.

Dienyl diketones containing tethered acetates selectively undergo two different 1,6-conjugate addition-initiated cyclization cascades. One is a 1,6-conjugate addition/cyclization sequence with incorporation of the nucleophile, and the other is catalyzed by DABCO and is thought to proceed via a cyclic acetoxonium intermediate. The reaction behavior of substrates lacking the tethered acetate was also studied. The scope of both types of cyclization cascades, the role of the amine additive, and the factors controlling reactivity and selectivity in the two different reaction pathways is discussed.

Citation

Joshua L Brooks, Alison J Frontier. Cyclization cascades initiated by 1,6-conjugate addition. Journal of the American Chemical Society. 2012 Oct 10;134(40):16551-3

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PMID: 23004564

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