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. Author manuscript; available in PMC: 2008 Aug 26.
Published in final edited form as: Chem Rev. 2007 May 27;107(6):2503–2545. doi: 10.1021/cr0509556

Table 49.

Conjugate addition of TMSCN to α,β-unsaturated imides.

graphic file with name nihms-63649-t0149.jpg
entry R methoda time (h) yield (%) ee (%)
1 Me A 26 92 98
2 Et A 26 95 97
3 n-Pr A 26 90 97
4 i-Pr A 26 91 94
5 i-Bu A 26 93 96
6 (CH2)3CH=CH2 A 48 96 95
7 i-Bu B 48 90 97
8 CH2OBn B 48 70 87
a

Reactions were carried out on a 0.5 mmol scale. Method A: 10 mol% (S,S)-(salen)Al-Cl, 2.5 equiv of TMSCN, 2.5 equiv 2-propanol, 0.2 mL of toluene, 24 °C. Method B: 15 mol% (S,S)-(salen)Al-Cl, 4 equiv of TMSCN, 4 equiv 2-propanol, 0.4 mL of toluene, 24 °C.