Strain-Driven Direct Cross-Aldol and -Ketol Reactions of Four-Membered Heterocyclic Ketones

 Zoltán Dobi, Tamás Holczbauer, and Tibor Soós*

Org. Lett.201517 (11), pp 2634–2637


Owing to the ring strain and α-heteroatom effect, the four-membered heterocyclic ketones can undergo direct cross-aldol and -ketol reactions without the need for preformed enol or “enolate-like” intermediates. Besides the organocatalyzed cross-ketol addition onto their highly active carbonyl group, their ability to act as a nucleophilic donor has also been explored. As a result, a number of discrete aldol adducts were synthesized and the distinct reactivities were successfully combined into a double-aldol one-pot reaction.