A palladium/chiral amine co-catalyzed enantioselective dynamic cascade reaction: synthesis of polysubstituted carbocycles with a quaternary carbon stereocenter

Guangning Ma; Samson Afewerki; Luca Deiana; Carlos Palo-Nieto; Leifeng Liu; Junliang Sun; Ismail Ibrahem; Armando Córdova

doi:10.1002/anie.201300559

A palladium/chiral amine co-catalyzed enantioselective dynamic cascade reaction: synthesis of polysubstituted carbocycles with a quaternary carbon stereocenter

Angew Chem Int Ed Engl. 2013 Jun 3;52(23):6050-4. doi: 10.1002/anie.201300559. Epub 2013 Apr 25.

Authors

Guangning Ma¹, Samson Afewerki, Luca Deiana, Carlos Palo-Nieto, Leifeng Liu, Junliang Sun, Ismail Ibrahem, Armando Córdova

Affiliation

¹ Department of Natural Sciences, Engineering and Mathematics, Mid Sweden University, 85170 Sundsvall, Sweden.

PMID: 23620447
DOI: 10.1002/anie.201300559

Abstract

Polysubstituted 5- and 6-membered carbocycles were synthesized by the title reaction. The one-pot dynamic relay process generates four new stereocenters, including a quaternary carbon center, in a highly enantioselective fashion (99.5:0.5→99:0.5 e.r.) by using a simple combination of palladium and chiral amine co-catalysts.

MeSH terms

Aldehydes
Amines / chemistry*
Catalysis
Cyclization
Hydrocarbons, Cyclic / chemical synthesis*
Hydrocarbons, Cyclic / chemistry
Molecular Structure
Palladium / chemistry*
Protein Structure, Quaternary
Stereoisomerism

Substances

Aldehydes
Amines
Hydrocarbons, Cyclic
Palladium