beta-Acyloxysulfonyl tethers for intramolecular Diels-Alder cycloaddition reactions.
[reaction: see text]. beta-Hydroxy sulfone-based tethers were employed for the first time to achieve thermally mediated intramolecular Diels-Alder cycloaddition. The reactions proceeded with complete regioselectivity and high (10/1) to complete endo/exo-selectivity and resulted in the preferential formation of one of the two possible endo-cycloadducts. The yields and stereoselectivities were proportional to the bulk of the R(1) substituent on the beta-acyloxysulfonyl tether.
Chumachenko
Nataliya
N
Department of Chemistry, Kent State University, Ohio 44242, USA.
Sampson
Paul
P
Hunter
Allen D
AD
Zeller
Matthias
M