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. Author manuscript; available in PMC: 2010 Dec 1.
Published in final edited form as: Synlett. 2009 Jan 1;2009(3):377–383. doi: 10.1055/s-0028-1087555

Table 2.

Optimization of Acyl Anion Additions to Aldehydes

graphic file with name nihms248673t2.jpg
Entry Fluoride source Aldehyde (equiv) Solvent Temp (°C) Yield (%)
  1 Me4NF 2 CH2Cl2 (0.2 M) 0 to 23 38
  2 Me4NF 1 CH2Cl2 (0.2 M) 0 to 23 27
  3 Me4NF 4 CH2Cl2 (0.2 M) 0 to 23 64
  4 Me4NF 4 CH2Cl2 (0.2 M) 0 to 23 58a
  5 Me4NF 4 CH2Cl2 (0.2 M) 23 61
  6 CsF 4 CH2Cl2 (0.2 M) 23 38
  7 CsF 4 DMF (0.2 M) 23 64
  8 CsF 4 i-PrOH (0.2 M) 23 70
  9 Me4NF 4 i-PrOH (0.2 M) 23 48
10 CsF 2 i-PrOH (1 M) 23 39
11 CsF 2 i-PrOH (0.4 M) 23 52
a

Three equiv i-PrOH added.