Chemistry and Physics Faculty Articles
Title
Direct Enantio‐ and Diastereoselective Oxidative Homocoupling of Aldehydes
Document Type
Article
Publication Date
10-1-2018
Publication Title
Chemistry - A European Journal
Keywords
Density functional calculations, Hammett analysis, Organocatalysis, Oxidative coupling of aldehydes, Pyrrolidines
ISSN
1521-3765
Volume
24
Issue/No.
55
First Page
14844
Last Page
14848
Abstract
A novel strategy for the direct enantioselective oxidative homocoupling of α‐branched aldehydes is presented. The methodology employs open‐shell intermediates for the construction of chiral 1,4‐dialdehydes by forming a carbon–carbon bond connecting two quaternary stereogenic centers in good yields and excellent stereoselectivities for electron‐rich aromatic aldehydes. The 1,4‐dialdehydes were transformed into synthetically valuable chiral pyrrolidines. Experimental mechanistic investigations based on competition experiments combined with computational studies indicate that the reaction proceeds through a radical cation intermediate and that reactivity and stereoselectivity follow different trends.
NSUWorks Citation
Næsborg, L., Leth, L. A., Reyes-Rodriguez, G. J., Palazzo, T. A., Corti, V., & Jørgensen, K. A. (2018). Direct Enantio‐ and Diastereoselective Oxidative Homocoupling of Aldehydes. Chemistry - A European Journal, 24, (55), 14844 - 14848. https://doi.org/10.1002/chem.201803506. Retrieved from https://nsuworks.nova.edu/cnso_chemphys_facarticles/261
ORCID ID
0000-0002-0566-0820
ResearcherID
V-6501-2018
DOI
10.1002/chem.201803506
Comments
©2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim