pi-Facial stereoselectivity in Diels-Alder cycloadditions to 1-oxaspiro[4.5]deca-6,9-dien-8-one. The strong directive effect of ether oxygen in a cross-conjugated ketone setting.
[reaction: see text] The title compound 1, prepared from 1,4-cyclohexanedione monoethylene ketal, was treated with several reactive dienes, including diphenylisobenzofuran and 9,10-dihydro-11,12-dimethylene-9,10-ethanoanthracene. These [4 + 2] cycloadditions proceed with a strong kinetic bias for bonding to the dienophile from the direction syn to the tetrahydrofuranyl oxygen and consequently hold value in stereoselective synthesis.
Paquette
Leo A
LA
Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, USA. paquette.1@osu.edu
Shetuni
Brandon B
BB
Gallucci
Judith C
JC