An efficient Darzens reaction promoted by 1, 8-diazabicyclo[5.4.0]undec-7-ene (DBU). Issue 30 (25th July 2019)

• Record Type: Journal Article
• Authors: Luo, Juan; Hu, Lanfang; Zhang, Minghao; Tang, Qiang
• Is Part Of: Tetrahedron letters. Volume 60:Issue 30(2019)
• Page Start: 1949
• Page End: 1951
• Publication Date: 2019-07-25
• Subjects: DBU -- Darzens reaction -- α, β-Epoxy ketone -- α-Haloketone; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.06.034
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: DBU promoted Darzens reaction with the α -haloketones containing an enolizable α ′-hydrogen as starting materials. Highlights: Darzens reaction with the α-haloketones containing an enolizable α ′-hydrogen as starting materials. The reaction proceeds with high diasteroselectivity. Without using any transition metals or additives. Abstract: An efficient DBU promoted Darzens reaction utilising α-haloketones containing an enolizable α′-hydrogen is reported. This method diastereoselectively afforded the corresponding α, β -epoxy ketones good to excellent yields in an one-pot reaction without using any transition metals or additives. Furthermore, haloketones without an α ′-hydrogen are also applicable in this reaction.