Enantioselective Construction of Quaternary Stereogenic Centers by the Addition of an Acyl Anion Equivalent to 1,3-Dienes.
Journal Article (Journal Article)
We report the enantioselective formation of quaternary stereogenic centers by the intermolecular addition of malononitrile, an acyl anion equivalent, and related pronucleophiles to several 1,3-disubstituted acyclic 1,3-dienes in the presence of a Pd-PHOX catalyst. Products are obtained in up to 88% yield and 99:1 er and in most cases are formed as a single regioisomer. The products' malononitrile unit undergoes oxidative functionalization to afford β,γ-unsaturated carbonyls bearing internal olefins and α-quaternary stereogenic centers.
- Adamson, NJ; Park, S; Zhou, P; Nguyen, AL; Malcolmson, SJ
- March 2020
Volume / Issue
- 22 / 5
Start / End Page
- 2032 - 2037
Electronic International Standard Serial Number (EISSN)
International Standard Serial Number (ISSN)
Digital Object Identifier (DOI)