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Wise, L.D.12
Zhi-Su, T.13
Weber, M.L.14
Wustrow, D.J.15
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23
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17444425377
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Additionally, benzhydrylamine and p-methoxybenzylamine were used as nucleophiles to give allylamines with excellent enantio- and regioselectivities. The allyamines were transformed into N-(3-methylacryloyl)-amines F, which were subjected to RCM to furnish lactams G;
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Diacylamides 3 are somewhat sensitive to acidic conditions. In particular, lengthy chromatographic processes using silica cause lowering of yield TBD: 1,5,7-triazabicyclo-[4.4.0]dec-5-ene For L1 ca. 2 h are optimal, while for L2 ca. 5 min are sufficient, cf.
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HPLC Data for 3 (Table 1), Daicel columns, 250 × 4.6 mm, 5 m with guard cartridge, 10 × 4 mm, 0.5 mL min-1; 3a: Chiralcel OD-H, n-hexane/i-PrOH 99.9: 0.1, rt, 220 nm, tR[(-)-(S)- 3a] = 19 min, tR[(+)-(R)- 3a] = 21 min; 3b: Chiralcel OD-H, n-hexane/i-PrOH 99.9: 0.1, rt, 220 nm, tR [3b] = 16 min and 19 min; 3c: Chiralcel AD-H, n-hexane/i-PrOH 98: 2, rt, 220 nm, tR[(+)- 3c] = 10 min, t R[(-)- 3c] = 11 min; 3d: Chiralcel OD-H, n-hexane/i-PrOH 99: 1, rt, 210 nm, tR[(+)- 3d] = 11 min, tR[(-)- 3d] = 18 min An exception is the compound 5, R = 2-furyl, which was formed with complete racemisation Several related amides F (R′ = CH3 and Σ = Bn or p-MeOC6H4) were also subjected to RCM. Double bond isomerisation was only found in the case R = n-Pr, likely caused by residual Ru compounds in the products, cf.
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