-Acetyl 1,3-propanediol serves as an acrolein proelectrophile in π-allyliridium-,-benzoate-catalyzed carbonyl allylations mediated by racemic α-substituted allylic acetates. Using the iridium catalyst modified by ()-SEGPHOS, a variety of 3-hydroxy-1,5-hexadienes are formed with uniformly high levels of regio-, -diastereo-, and enantioselectivity.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10425987 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.3c01022 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Acetyl 1,3-Propanediol as an Acrolein Proelectrophile in Enantioselective Iridium-Catalyzed Carbonyl Allylation.
Org Lett
May 2023
University of Texas at Austin, Department of Chemistry, Austin, Texas 78712, United States.
-Acetyl 1,3-propanediol serves as an acrolein proelectrophile in π-allyliridium-,-benzoate-catalyzed carbonyl allylations mediated by racemic α-substituted allylic acetates. Using the iridium catalyst modified by ()-SEGPHOS, a variety of 3-hydroxy-1,5-hexadienes are formed with uniformly high levels of regio-, -diastereo-, and enantioselectivity.
View Article and Find Full Text PDFAllyl Alcohol as an Acrolein Equivalent in Enantioselective C-C Coupling: Total Synthesis of Amphidinolides R, J, and S.
J Am Chem Soc
April 2023
Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States.
The first systematic study of catalytic enantioselective 1,2-additions to acrolein is described. Specifically, using allyl alcohol as a tractable, inexpensive acrolein proelectrophile, iridium-catalyzed acrolein allylation is achieved with high levels of regio-, -diastereo-, and enantioselectivity. This process delivers 3-hydroxy-1,5-hexadienes, a useful compound class that is otherwise challenging to access via enantioselective catalysis.
View Article and Find Full Text PDFA QSAR study of the acute toxicity of some industrial organic chemicals to goldfish. Narcosis, electrophile and proelectrophile mechanisms.
Xenobiotica
August 1987
US Environmental Protection Agency, Office of Toxic Substances, Washington, DC 20460.
1. A baseline toxicity QSAR model was derived for the 24-h LC50 to the goldfish, Carassius auratus. 2.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!