Supporting Information
Optically active helical polymers with pendent thiourea groups: chiral organocatalyst
for asymmetric Michael addition reaction
Haiyang Zhang, Wantai Yang and Jianping Deng*
State Key Laboratory of Chemical Resource Engineering, College of Materials Science and
Engineering, Beijing University of Chemical Technology, Beijing 100029, China
Figure S1. FT-IR spectra of (a) 1-phenylethylamine, (b) 1-phenylethyl isothiocyanate, and (c)
N-propargylthiourea monomer (M1) (in KBr tablet).
Figure S2. 1H NMR spectrum of N-propargylthiourea monomer (M1), measured in CDCl3 at
r.t.
Figure S3. FT-IR spectra of (a) monomer 1 and (b) monomer 2; copolymer of (c)
M10.1-co-M20.9 and (d) M10.2-co-M20.8 (in KBr tablet).
Figure S4. 1H NMR spectrum of poly(M10.2-co-M20.8), measured in DMSO-d6 at r.t.
Figure S5. (A) CD and (B) UV-vis spectra of poly(M1S0.1-co-M20.9) in CH2Cl2 (0 °C and
25 °C), CHCl3, DMF and MeOH (25 °C).
Figure S6 FT-IR spectra of (a) trans-β-nitrostyrene, (b) diethyl malonate and (c) Michael
adduct catalyzed by chiral helical copolymers (in KBr tablet).
Figure S7. 1H NMR spectrum of Michael adduct catalyzed by chiral helical copolymers,
measured in CDCl3 at r.t.
Figure S8.
13
C NMR spectrum of Michael adduct catalyzed by chiral helical copolymers,
measured in CDCl3 at r.t.
Figure S9. Typical HPLC spectrum of Michael adduct catalyzed by poly(M1R0.1-co-M20.9).
Figure S10. Typical HPLC spectrum of Michael adduct catalyzed by poly(M1S0.1-co-M20.9).
Figure S11 (A) CD and (B) UV-vis spectra of Michael adduct catalyzed by (a)
poly(M1R0.1-co-M20.9) and (b) poly(M1S0.1-co-M20.9).