K. Fuji et al., DIASTEREOSELECTIVE DIELS-ALDER CYCLOADDITIONS WITH CHIRAL 1-(ALKYLSULFINYL)-2-NITROALKENES, Journal of organic chemistry, 59(8), 1994, pp. 2211-2218
Several chiral 2-nitro-1-sulfinylalkenes were prepared and examined fo
r their utility as dienophiles for asymmetric [4 + 2] cycloaddition. T
risubstituted dienophiles 3-6 undergo diastereoselective cycloaddition
with cyclopentadiene in the presence of Lewis acids. Even the tetrasu
bstituted chiral sulfinyl dienophiles 1 and 2 could be coerced into un
dergoing [4 + 2] cycloaddition to afford the cycloadducts in high yiel
d without concomitant elimination if the reaction was conducted under
high pressure. Generally, the Z-sulfinyl dienophiles 1-4 showed higher
diastereo- and endo/exo-selectivity than;the E-dienophiles 5 and 6.