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. Author manuscript; available in PMC: 2011 Jan 14.
Published in final edited form as: J Am Chem Soc. 2008 Jun 17;130(27):8726–8732. doi: 10.1021/ja800250q

Table 1.

Solvent-dependent E/Z selectivities resulting from the enolization of ketone 5 (eq 3)a

solvent, S
 E-6:Z-6
Et3N 110:1
Me2NEt 90:1
(i-Pr)2NEt 40:1
i-Bu3N 60:1
THF (0.5 M) 13:1
THF (10 M) 1:13
Me4THFb 40:1
TMEDA 30:1
a

[5] = 0.050 M; [LiHMDS] = 0.15 M; [S] = 1.5 M in toluene; −78 °C.

b

Me4THF = 2,2,5,5-tetramethyltetrahydrofuran (1.5 M in toluene).