Synthesis of heterocyclic systems with a carbohydrate fragment

Cathodically Promoted Stereoselective Addition of 1,3-Dinitro Compounds to Levoglucosenone

“…As pointed out earlier, ring-forming reactions of several other classes of compounds with 1 have been achieved with catalysis by chemical bases such as triethylamine and piperidine. [18][19][20] Compared to these reactions, our preparations generally gave higher yields. It will be interesting to see if the electrochemical method will also be superior for additions to 1 of amides of ␣-nitrocarboxylic 131.81, 131.77, 131.45, 130.95, 130.83, 129.27, 129.24, 127.82, 127.28, 125.31, 124.78, 123.92, 123.11, 122.65.…”

“…acids, urea, thiourea, and guanidines, and 1,3-dicarbonyl compounds, compared to procedures that make use of chemical bases. [18][19][20] …”

Bio‐Based Chiral Amines via Aza‐Michael Additions to (–)‐Levoglucosenone Under Aqueous Conditions

“…Previous aza-Michael reactions to LGO are shown in Scheme 1. [15] An elegant heteroannulation was observed when aromatic bisnucleophiles were employed; [17,18] an initial conjugate addition followed by reaction at the carbonyl affords interesting N-containing scaf-Scheme 1. [14] Semenov, Evans and co-workers reported the aza-Michael addition of various azoles to LGO to give 3, which in some instances also formed a diol 4 resulting from carbonyl hydration (Scheme 1, B).…”

“…Eiden and co-workers reported an aza-Michael addition of aniline and 2-bromoaniline to LGO to give 2a and 2b in poor yield (Scheme 1, A). [14][15][16][17][18] Eur. [15,16] The same paper reported the aza-Michael addition of imides and saccharin to LGO and that the yield of some reactions can be increased using cathodic electrolysis.…”

Reactions of 3-iodolevoglucosenone with sodium derivatives of some CH acids. Chiral cyclopropanes and stable oxetenes

“…and (IS,2R,6R,SR)-4-methyl-7-oxo-5,9,11-trioxatricydo[6.2.1.0z,6]undec-3(L~-eae-3-carboxylate (15) were prepared in 42 and 40% yields, respectively by the procedure described above at a 3 : ethyl aeetoacetate ratio of I : 1 and a temperature of -60 *C. Eaol ketol 14. Rf 0.50 (AeOEt--heptane, 7 : 3), m.p.…”