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. Author manuscript; available in PMC: 2014 Jan 27.
Published in final edited form as: J Org Chem. 2013 Jan 10;78(2):410–418. doi: 10.1021/jo302211f

Table 1. Aldol addition of diketone 4 via pathways a and b.

graphic file with name nihms434702u1.jpg
entry reagent ia isolated yield (%)
8 9 10 11
1 TFA 45 0 40 0
2 NaH 56 0 6 0
3 Pyrrolidine 80 0 8 0
4 LDA 71 0 22 0
5 LiHMDS 65 0 25 0
6 LiTMP 48 0 43 0
7 Ph3CLi 79 0 5 0
8 Al2O3 81 7 0 0
9 TiCl4 50 0 32 0
a

See Experimental Section for detailed experimental procedures