Low temperature n-butyllithium-induced [3,3]-sigmatropic rearrangement/electrophile trapping reactions of allyl-1,1-dichlorovinyl ethers. Synthesis of β-, γ- and δ-lactones

Aaron Christopher; Dahniel Brandes; Stephen Kelly; Thomas G Minehan

doi:10.1039/c3ob41777h

Low temperature n-butyllithium-induced [3,3]-sigmatropic rearrangement/electrophile trapping reactions of allyl-1,1-dichlorovinyl ethers. Synthesis of β-, γ- and δ-lactones

Org Biomol Chem. 2013 Nov 28;11(44):7658-61. doi: 10.1039/c3ob41777h. Epub 2013 Oct 10.

Authors

Aaron Christopher¹, Dahniel Brandes, Stephen Kelly, Thomas G Minehan

Affiliation

¹ Department of Chemistry and Biochemistry, California State University, Northridge, 18111 Nordhoff Street, Northridge, CA 91330, USA. [email protected].

Abstract

Treatment of allyl-1,1-dichlorovinyl ethers with n-BuLi at -78 °C, followed by quenching with ketones, epoxides, and oxetanes, leads to highly substituted β-, γ-, and δ-lactones in good to excellent yields.

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Cold Temperature*
Ethers / chemistry*
Lactones / chemical synthesis*
Organometallic Compounds / chemistry*

Substances

Ethers
Lactones
Organometallic Compounds
n-butyllithium

Abstract

Publication types

MeSH terms

Substances

Grants and funding