Enantioselective Synthesis of α-Amino Acids and Monosubstituted 1,2-Diamines by Conjugate Addition of 4-Phenyl-2-oxazolidinone to Nitroalkenes

Synthesis of Nonulosonic Acids

“…Swern oxidation of the so formed alcohol afforded aldehyde 66 in 87 % yield over five steps. Next, the first chain elongation was carried out via nitroaldol reaction between 66 and the known nitro derivative 67 [ 24 ] by treatment with TBAF in THF at –50 °C to obtain the desired d ‐rhamno substrate 68 in 34 % overall yield. The low yield of 68 in nitroaldol reaction was attributed to the use of a racemic mixture of nitro derivative 67 and the authors proposed that the remaining adduct which would have formed from ' S ' isomer of 67 could potentially lead to the l ‐gulo derivative which in turn would finally provide naturally occurring 8‐ epi ‐legionaminic acid 6 .…”

Vicinal Diamino Functionalities as Privileged Structural Elements in Biologically Active Compounds and Exploitation of their Synthetic Chemistry

“…In this method, a nitroalkane is added to an aldehyde in the presence of a base and the resulting nitroalkene is subjected to a nucleophilic addition with a chiral nucleophile. Final reduction of the nitro group gave the diamine in good yields and enantioselectivity (Scheme 6) (25).…”

Tandem driven dynamic combinatorial resolution via Henry–iminolactone rearrangement

“…Reduction of the nitro group and further hydrolysis of the lactam, would lead to these structures which are of broad utility, reaching from antitumor reagents to ligands in stereoselective organic synthesis. [22][23][24] More detailed time-dependent NMR-studies of the process with aldehyde 1 were subsequently performed in order to evaluate the tandem reaction (Fig. 4).…”