- Journal
- JOURNAL OF ORGANIC CHEMISTRY
- Année
- 2017
- Volume
- 82
- Numéro
- 7
- Pages
- 3965-3975
- Mois
- APR 7
- DOI
- 10.1021/acs.joc.7b00197
Abstract
A one-pot difluorocyclopropenation/Ireland-Claisen rearrangement sequence applied to readily available R propargyl glycolates was developed as a route toward functionalized alkylidene(gem-difluorocyclopropanes). This strategy conveniently avoids the isolation of the unstable 3,3-difluorocydopropenylcarbinyl glycolates arising from the difluorocyclopropenation. The Ireland-Claisen rearrangement proceeds with high diastereoselectivity and chirality transfer to afford alkylidene(gem-difluorocyclopropanes) incorporating a quaternary stereocenter and a protected glycolic acid moiety, which are useful building blocks for the preparation of functionalized gem-difluorocydopropanes.