An intramolecular [2 + 2] cycloaddition of ketenimines via palladium-catalyzed rearrangements of N-allyl-ynamides.
A cascade of Pd-catalyzed N-to-C allyl transfer-intramolecular ketenimine-[2 + 2] cycloadditions of N-allyl ynamides is described. This tandem sequence is highly stereoselective and the [2 + 2] cycloaddition could be rendered in a crossed or fused manner depending on alkene substitutions, leading to bridged and fused bicycloimines.
Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53705, USA.
Kyle A
KA
DeKorver
Richard P
RP
Hsung
Wang-Ze
WZ
Song
Xiao-Na
XN
Wang
Mary C
MC
Walton
D000577:Amides / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005030:Ethylenes / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D001643:Bridged Bicyclo Compounds; D005030:Ethylenes; D007097:Imines; D007659:Ketones; D010165:Palladium; C008223:ketene