Catalytic, enantioselective bifunctional inverse electron demand hetero-Diels-Alder reactions of ketene enolates and o-benzoquinone diimides.
In this Communication, we report a system in which an achiral Lewis acid (activating the diene) works in concert with a chiral nucleophile (dienophile) to effect the first highly enantio- and regioselective catalytic inverse electron demand Diels-Alder [4 + 2] cycloaddition reaction to form biologically active quinoxalinones from ketene enolates and o-benzoquinone diimides in good to excellent yields with >99% ee.
Abraham
Ciby J
CJ
Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, MD 21218, USA.
Paull
Daniel H
DH
Scerba
Michael T
MT
Grebinski
James W
JW
Lectka
Thomas
T
D000438:Alcohols / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D016227:Benzoquinones / Q000737:chemistry*; D002384:Catalysis; D004583:Electrons; D005030:Ethylenes / Q000737:chemistry*; D007094:Imides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008956:Models, Chemical; D013237:Stereoisomerism
D000438:Alcohols; D000466:Alkadienes; D016227:Benzoquinones; D005030:Ethylenes; D007094:Imides; D007659:Ketones; C008223:ketene