Se. Denmark et Lr. Marcin, NITROALKENE [4-DISUBSTITUTED AND 3,4-DISUBSTITUTED PYRROLIDINES(2] CYCLOADDITION AS A GENERAL AND STEREOSELECTIVE ROUTE TO THE SYNTHESIS OF3,3), Journal of organic chemistry, 58(15), 1993, pp. 3857-3868
2,2-Disubstituted 1-nitroalkenes 12 undergo Lewis acid-promoted [4 + 2
] cycloadditions with n-butyl vinyl ether to afford cyclic nitronates
14 as anomeric mixtures in good yields. The resulting nitronates were
reduced with hydrogen in the presence of Adam's catalyst to afford 3,3
-disubstituted pyrrolidines which were isolated in good yield as their
N-p-toluenesulfonamides 17. Cycloadditions of (E)-2-nitrostyrene with
ethyl (E)- and (Z)-1-propenyl ethers provided for the stereoselective
synthesis of cis- and -3-phenyl-4-methyl-N-(p-tolylsulfonyl)pyrrolidi
ne. Similarly, trans-3,4-diphenyl-N-(p-tolysulfonyl)pyrrolidine was pr
epared from (E)-2-nitrostyrene and ethyl (E)-2-styryl ether.