Syntheses of supposed and real pillarose

Synthetic applications of the photochemically induced addition of oxycarbinyl species to α-enones. Part II. The addition of ketals, aldehydes, and polyfunctional species

“…Other projects in our laboratory (2) required that the synthetic potential of these reactions be explored. In contemplating the utility of these products we were mindful of the recent work of Schlessinger and co-workers (3) who have shown that 1,4-dicarbonyl species can be extremely versatile synthons.…”

“…Ethylene glycol, propane-1,3-diol, methyl hydracrylate, and methyl glycollate were chosen as polyfunctional alcohols for the studies summarized in Table 1 (entries [1][2][3][4]. With ethylene glycol and the enone la, the ketodiol 3a was Can.…”

Direct synthesis of .alpha.-halogenomethyl-.alpha.-amino acids from the parent .alpha.-amino acids

“…Methyl 2-(benzylideneamino)-3-(4-hydroxyphenyl)propionate (6f): (70%) mp (CH2Cl2/pentane) 100 °C; NMR (CDC13) 2.85-3.30 (m, 2, -CH2-), 3.68 (s, 3, C02CH3), 4.15 (m, 1, >CHC02-), 5.65 (broad s, 1, OH), 6.6-7.0 (m, 4, C6H4-), 7.20-7.75 (m, 5, C6H5C=N-), 7.90 (s, 1, CH=N); IR (Nujol) 3460, 1708, 1645 cm"1.…”

“…Hz, -CHF2), 7.14-7.81 (m, 10, C6H5-), 8.17 (s, 1, -CH=N-), 8.32 (s, 1, -CH=N-); 19F NMR (CDC13) -129.4 [AB part ofanABX system (4 lines), JHp = 54. 5 Hz],…”

The past, present, and future of the Yang reaction

“…18 He later achieved the synthesis of pillarose with this C–H functionalization reaction. 19 UV-irradiation of enone 32 in the presence of 16 mol% of 10 and a large excess of ethylene glycol gave δ-lactone 33 (Fig. 5).…”