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. 2015 Jul 14;6(10):5904–5912. doi: 10.1039/c5sc02144h

Table 3. Base screen for basicity and steric effects a .

Base Δ-1
% ee b % yield of (S)-10 c pKa d
DBU 34 20 24.33
NEt3 72 55 18.82
DIEA 70 38 18.80
graphic file with name c5sc02144h-u2.jpg 53 33 18.64
graphic file with name c5sc02144h-u3.jpg 66 43 18.62
DABCO 66 44 18.29
DMAP 57 21 17.95
graphic file with name c5sc02144h-u4.jpg 40 17 15.8
Collidine 10 8 14.77
graphic file with name c5sc02144h-u5.jpg 0 21 13–14
TBAF 20 61 ?

aAll reactions were performed using β-nitrostyrene 8 (0.34 mmol, 1 equiv.), diethylmalonate 9 (0.68 mmol, 2 equiv.), and base (0.034 mmol, 0.1 equiv.) in MeCN (1 mL) with 5 mol% catalyst (Δ-1) at room temperature for 24 h.

bDetermined by chiral HPLC analysis.

cIsolated yields.

dpKa of conjugate acid in acetonitrile.38