DBU-Catalyzed Ring-Opening and Retro-Claisen Fragmentation of Dihydropyranones
Artikel i vetenskaplig tidskrift, 2020

We present a general protocol for the formal Michael addition of acetone to alpha,beta-unsaturated esters and amides, a transformation difficult to perform using current methods. The protocol comprises of an amidine catalyzed relay ring-opening and fragmentation of 3,4-dihydropyranones. The reaction proceeds under mild conditions, has a broad substrate scope and the products can be isolated in good to excellent yields. The method can be applied to homochiral substrates with total preservation of chiral information, generating products in high optical purity. Kinetic experiments supported by quantum chemical modeling indicate a mechanism in which the catalyst takes a bifunctional role, acting both as a Bronsted base and as a hydrogen-bond donor.

Organocatalysis

Retro-claisen

Oxygen heterocycles

Synthetic methods

Michael addition

Författare

Anton Axelsson

Chalmers, Kemi och kemiteknik, Kemi och biokemi, Fysikalisk kemi

Emmelie Hammarvid

Student vid Chalmers

Martin Rahm

Chalmers, Kemi och kemiteknik, Kemi och biokemi

Henrik Sunden

Göteborgs universitet

European Journal of Organic Chemistry

1434-193X (ISSN)

Vol. 2020 33 5436-5444

Ämneskategorier

Annan kemiteknik

Biokatalys och enzymteknik

Organisk kemi

DOI

10.1002/ejoc.202000858

Mer information

Senast uppdaterat

2020-10-30