An efficient organocatalytic cascade reaction has been developed involving a Michael-hemiaminalization relay for the asymmetric synthesis of spiropiperidinone derivatives : bearing adjacent quaternary and tertiary chiral centers via LUMO or HOMO activation. Importantly, this methodology demonstrates that applying distinct activation modes to different substrates in the same reaction can diverge diastereoselectivity. To our knowledge, this is also one of the few published cases of primary amine catalytic [3 + 3] cycloaddition reactions involving alpha-branched beta-ketoamides.
Key words: CARBON QUATERNARY STEREOCENTERS; CONTIGUOUS STEREOGENIC CENTERS; BETA-KETOCARBONYLS; MICHAEL ADDITION; PRIMARY AMINE; ENAMINE CATALYSIS; ALPHA-ALLYLATION; DUAL CATALYSIS; NONADJACENT STEREOCENTERS; 1,3-DICARBONYL COMPOUNDS
引用本文： . . 华西虚拟期刊, 2000, 1(1): 397-406-. doi: 10.1021/acs.joc.6b02489 复制