Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles.
Publication
, Journal Article
Adamson, NJ; Wilbur, KCE; Malcolmson, SJ
Published in: Journal of the American Chemical Society
February 2018
We report a highly enantioselective Pd-PHOX-catalyzed intermolecular hydroalkylation of acyclic 1,3-dienes. Meldrum's acid derivatives and other activated C-pronucleophiles, such as β-diketones and malononitriles, react with a variety of aryl- and alkyl-substituted dienes in ≤20 h at room temperature. The coupled products, obtained in up to 96% yield and 97.5:2.5 er, are easily transformed into useful chemical building blocks for downstream synthesis.
Duke Scholars
Published In
Journal of the American Chemical Society
DOI
EISSN
1520-5126
ISSN
0002-7863
Publication Date
February 2018
Volume
140
Issue
8
Start / End Page
2761 / 2764
Related Subject Headings
- Temperature
- Stereoisomerism
- Palladium
- Nitriles
- Molecular Structure
- Ketones
- General Chemistry
- Catalysis
- Alkylation
- Alkadienes
Citation
APA
Chicago
ICMJE
MLA
NLM
Adamson, N. J., Wilbur, K. C. E., & Malcolmson, S. J. (2018). Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles. Journal of the American Chemical Society, 140(8), 2761–2764. https://doi.org/10.1021/jacs.7b13300
Adamson, Nathan J., Katherine C. E. Wilbur, and Steven J. Malcolmson. “Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles.” Journal of the American Chemical Society 140, no. 8 (February 2018): 2761–64. https://doi.org/10.1021/jacs.7b13300.
Adamson NJ, Wilbur KCE, Malcolmson SJ. Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles. Journal of the American Chemical Society. 2018 Feb;140(8):2761–4.
Adamson, Nathan J., et al. “Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles.” Journal of the American Chemical Society, vol. 140, no. 8, Feb. 2018, pp. 2761–64. Epmc, doi:10.1021/jacs.7b13300.
Adamson NJ, Wilbur KCE, Malcolmson SJ. Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles. Journal of the American Chemical Society. 2018 Feb;140(8):2761–2764.
Published In
Journal of the American Chemical Society
DOI
EISSN
1520-5126
ISSN
0002-7863
Publication Date
February 2018
Volume
140
Issue
8
Start / End Page
2761 / 2764
Related Subject Headings
- Temperature
- Stereoisomerism
- Palladium
- Nitriles
- Molecular Structure
- Ketones
- General Chemistry
- Catalysis
- Alkylation
- Alkadienes