The Michael reaction, a nucleophilic addition to a conjugated unsaturated C=C bond, is also employed in the synthesis of sultams. An illustrative example is the enantioselective synthesis of bicyclic sultams 120 through a double consecutive Michael addition (Table ). The diatomic aminomethyl component for the construction of the future bicyclic sultam is provided by the nitrile group of hex-5-ene nitrile (121). The synthetic pathway involves reducing the nitrile fragment to the corresponding CH2NH2-substituent, which is then sulfonylated with 2-chloroethane sulfonyl chloride to introduce the vinyl sulfone fragment. The conjugated enones 122 are obtained through the cross-metathesis reaction of vinyl sulfonamide 123. These enones 122 undergo an intramolecular asymmetric aza-Michael with cyclization to form piperidines 124 by using quinine derivative 125 as a catalyst. The nitrile group can also serve as a precursor of the amide fragment in the synthesis of bicyclic sultams. For instance, hydroxysultam 127 can react with trichloroacetonitrile 128 through the formation of imidate, followed by the intramolecular Michael addition to produce oxazoline 129. The subsequent treatment of compound 129 with trifluoroacetic acid leads to the formation of acylated amino alcohol 130 (Scheme 17).