Table 1.

Double-Michael Reactions of the Amidophenol 1a and the Allene 2b Mediated by Different Bases^a

entry	baseb	pKa(H2O)c	nucleophilicity d	yield(%)e
1	PMe3	8.7	15.49f	86
2	quinuclidin e	11.3	20.54g	26
3	3-HQD	9.9		54
4	DABCO	8.7	18.80g	77
5	DMAP	9.2	15.80h (14.95)g	82
6	Na2CO3	10.3		35
7	NaHCO3	6.3		16
8	NaOAc	4.8		53

^aReactions were performed using 0.4 mmol of 1a and 1.1 equiv of 2b.

^bFor the complete list of bases tested, see the Supporting Information.

^cReference 14.

^dReference 15.

^eIsolated yield.

^fThe value is the nucleophilicity of PBu₃ (in CH₂Cl₂).

^gNucleophilicity in MeCN.

^hNucleophilicity in CH2Cl2.