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


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

Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, 1519 Budapest, Hungary
Org. Lett., Article ASAP
DOI: 10.1021/acs.orglett.5b01002

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.

Budapest, Hungary

Budapest is the largest city and also the capital of Hungary. It is the principal transportation, industrial, commercial, …

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