Practical access to highly enantioenriched quaternary carbon Michael adducts using simple organocatalysts.
A three component catalyst system entailing an amino acid (O(t)Bu-L-threonine), a hydrogen bond donor (sulfamide), and an amine base (DMAP) allows α-branched aldehyde addition to nitroalkenes in good to high yield and excellent ee. Importantly, the lowest reported catalyst loading (5.0 mol%) and aldehyde stoichiometry (1.2-2.0 equiv) is demonstrated and in most instances the best current product profile is observed.
Nugent
Thomas C
TC
Department of Chemistry, School of Engineering and Science, Jacobs University Bremen, Campus Ring 1, 28759 Bremen, Germany. t.nugent@jacobs-university.de
Shoaib
Mohammad
M
Shoaib
Amna
A
D000447:Aldehydes / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D006860:Hydrogen Bonding; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D002244:Carbon