Cooperative catalysis by carbenes and Lewis acids in a highly stereoselective route to gamma-lactams.
Enzymes are a continuing source of inspiration for the design of new chemical reactions that proceed with efficiency, high selectivity and minimal waste. In many biochemical processes, different catalytic species, such as Lewis acids and bases, are involved in precisely orchestrated interactions to activate reactants simultaneously or sequentially. This type of 'cooperative catalysis', in which two or more catalytic cycles operate concurrently to achieve one overall transformation, has great potential in enhancing known reactivity and driving the development of new chemical reactions with high value. In this disclosure, a cooperative N-heterocyclic carbene/Lewis acid catalytic system promotes the addition of homoenolate equivalents to hydrazones, generating highly substituted gamma-lactams in moderate to good yields and with high levels of diastereo- and enantioselectivity.
Raup
Dustin E A
DE
Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA.
Cardinal-David
Benoit
B
Holte
Dane
D
Scheidt
Karl A
KA
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006835:Hydrazones / Q000737:chemistry*; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis*
D000447:Aldehydes; D006835:Hydrazones; D047090:beta-Lactams