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. Author manuscript; available in PMC: 2011 Sep 29.
Published in final edited form as: J Am Chem Soc. 2010 Sep 29;132(38):13179–13181. doi: 10.1021/ja1061196

Table 1.

Conjugate Addition Optimizationa

graphic file with name nihms233585t1.jpg
entry base additive GC yield (%)c
1 Et3N – NR
2 KHMDS – 70
3 NaH – 60
4 n-BuLib – 88
5 n-BuLib 12-crown-4 74
6 n-BuLib LiCl (1 equiv) 95
a

Reactions run on 0.4 mmol scale.

b

A and base were combined in THF at −78 °C and warmed to 20 °C. THF was then removed under vacuum.

c

Determined by gas chromatography with dodecane as an internal standard.