Enantioselective Construction of Quaternary Stereogenic Centers by the Addition of an Acyl Anion Equivalent to 1,3-Dienes
Nathan J. Adamson, Sangjune Park, Pengfei Zhou, Andrew L. Nguyen and Steven J. Malcolmson*
*Department of Chemistry, Duke University, Durham, North Carolina 27708, United States,
Email: steven.malcolmson
duke.edu
N. J. Adamson, S. Park, P. Zhou, A. L. Nguyen, S. J. Malcolmson, Org. Lett., 2020, 22, 2017-2021.
DOI: 10.1021/acs.orglett.0c00412
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Abstract
An intermolecular addition of malononitrile and related pronucleophiles to several 1,3-disubstituted acyclic 1,3-dienes in the presence of a Pd-PHOX catalyst provides products with quaternary stereogenic centers in good yield, excellent er, and in most cases as a single regioisomer. The products undergo oxidative functionalization to afford β,γ-unsaturated carboxylic acid derivatives.
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Key Words
active methylene compounds, nitriles
ID: J54-Y2020
