Intramolecular Michael reactions of aliphatic aldehyde enolates generated by imidazolium carbenes

• Published in: Tetrahedron letters Vol. 52; no. 19; pp. 2468 - 2470
• Main Authors: Kim, Hyoungsu, Byeon, Seong Rim, Leed, Marina G.D., Hong, Jiyong
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 11.05.2011; Elsevier
• Subjects: Aldehyde enolate; Aldehydes; Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; Aliphatic compounds; Brønsted base; Carbenes; Carbonyl compounds; Chemical reactivity; Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Intramolecular Michael reaction; Michael reaction; N-heterocyclic carbene; Organic chemistry; Physical Sciences; Preparations and properties; Reactivity and mechanisms; Science & Technology; Synthesis (chemistry); Tetrahedrons; N-heterocyclic carbene; Intramolecular Michael reaction; Aldehyde enolate; Brønsted base; ALCOHOLS; BASICITY; N-HETEROCYCLIC CARBENES; Bronsted base; Michael addition; Intramolecular reaction; Organic cation; Aliphatic compound; Nitrogen heterocycle; Aldehyde; Unsaturated compound; Stereoselectivity; Carbonyl Compounds; Chemical reactivity; Chemical synthesis; Enolate; Acid medium; Cyclopentane derivatives
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2011.03.008

Due to the high reactivity of the formyl group under either basic or acidic reaction conditions required for the direct generation of aldehyde enolates, intramolecular Michael additions of aldehyde enolates to α,β-unsaturated carbonyl compounds have been underexplored for the stereoselective synthesis of carbocyclic compounds. The intramolecular Michael reaction of aldehyde enolates generated by imidazolium carbenes was explored for the synthesis of cyclopentane aldehydes. The imidazolium carbenes were used as Brønsted bases to directly generate the aldehydes enolates.