Diastereoselective synthesis of hydantoin- and isoxazoline-substituted dispirocyclobutanoids.
Synthetic strategies for constructing novel achiral cyclobutanoid isoxazolidinoimidazolidinedione heterocycles, with a generalized structure of II, have been developed via 1,3-dipolar cycloaddition and carbanilide cyclization transformations from methylenecyclobutane 13. The exo methylene cyclobutane system has made the realization of some diasteroselectivity possible, such that the H-bond (Boc-NH) directed product (i.e., 14) was obtained with 3:1 selectivity relative to the non-H-bond directed product (i.e., 15).
Park
K H
KH
Department of Chemistry, One Shields Avenue, University of California, Davis, California 95616, USA.
Kurth
M J
MJ
D018360:Crystallography, X-Ray; D003500:Cyclization; D006827:Hydantoins / Q000138:chemical synthesis*; D007555:Isoxazoles / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*
D006827:Hydantoins; D007555:Isoxazoles; D013141:Spiro Compounds