Biomaterial Database

Iridium-Catalyzed Enantioselective Formal α-Allylic Alkylation of Acrylonitrile. 2023

Pankaj Roy, and Santanu Mukherjee

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.

A highly enantioselective formal α-allylic alkylation of acrylonitrile is developed using 4-cyano-3-oxotetrahydrothiophene (c-THT) as a safe and easy-to-handle surrogate of acrylonitrile. This two-step process consists of an Ir(I)/(P,olefin)-catalyzed branched-selective allylic alkylation using easily accessible branched rac-allylic alcohols as the allylic electrophile followed by retro-Dieckmann/retro-Michael fragmentation and is shown to be applicable for the enantioselective synthesis of α-allylic acrylates as well as α-allylic acrolein.

UI	MeSH Term	Description	Entries
D007495	Iridium	A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D000181	Acrylonitrile	A highly poisonous compound used widely in the manufacture of plastics, adhesives and synthetic rubber.	Vinyl Cyanide,Cyanide, Vinyl
D000478	Alkylation	The covalent bonding of an alkyl group to an organic compound. It can occur by a simple addition reaction or by substitution of another functional group.	Alkylations
D000498	Allyl Compounds	Alkenes with the general formula H2C	Compounds, Allyl
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer