Table 1 α-Functionalization/aldol reactions with pentanal and dioxanone 13.

^aDiastereomeric ratio determined by ¹H NMR spectroscopic analysis of crude reaction mixture.
^b% isolated yield of diastereomer shown.
^cPentanal (1.0 equiv), L-pro (0.8 equiv), NCS (1.05 equiv), 13 (1.05 equiv), CH₂Cl₂, rt, 24 h.
^dPentanal (1.5 equiv.), L-pro (1.5 equiv), X⁺ source (1.5 equiv), NaHCO₃ (1.5 equiv.), DMF (0.75 M), 1.5 h, −10 °C then add 13 (1.0 equiv) in CH₂Cl₂, rt, 48 h.
^eCH₂Cl₂-DMF = 9:1.
^frt, 60 h.
^gPentanal (2.0 equiv.), L-pro (2.0 equiv), PhthN-SCF₃ (2.0 equiv), NaHCO₃ (2.0 equiv.), DMSO (0.75 M), 1.25 h, rt then add 13 (1.0 equiv.) in CH₂Cl₂, rt, 48 h (CH₂Cl₂-DMSO = 5:1).
^hPentanal (1.1 equiv.), L-Pro (0.8 equiv), CbzNNCbz (1.0 equiv), MeNO₂ (0.50 M), rt then add 13 (2.0 equiv), rt, 48 h.

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