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. Author manuscript; available in PMC: 2011 Mar 29.
Published in final edited form as: Angew Chem Int Ed Engl. 2010 Apr 1;49(15):2747–2749. doi: 10.1002/anie.200907076

Table 1.

Optimization of the triple aldol reaction.

graphic file with name nihms279227t1.jpg
Entry Solvent T
[°C]		 Additive
[mol%]		 Yield
of 2a [%][a]		 Yield
of 3a [%][a,b]
1 CH2Cl2 0 to 40 none 75   0
2 hexanes 23 to 65 none <5   0
3 toluene −78 to 80 none <5   0
4 PhCl 0 to 50 none 60 <5
5 C8F18 0 to 60 none 20 <5
6 CH2Cl2 0 to 23 ICH2CH2I (10) 37 31
7 CH2Cl2 −78 to 23 MeI (10) 71 13
8 CH2Cl2 −40 to 0 PhI (10) 30 52
9 CH2Cl2 −40 to 23 1,2-C6H4I2 (10) 49 27
10 CH2Cl2 −40 to 23 2-I-py (10) <5   0
11[c] CH2Cl2 −40 to 23 I2 (5.0) 65   7
12[c] CH2Cl2 −40 to 23 PhI (10) <5 85
13[c] CH2Cl2 −40 to 0 PhI (10) 64 32
14[c] CH2Cl2 0 PhI (10) 29 51
15[c] CH2Cl2 23 PhI (10) 15 47
16[c] CH2Cl2 −40 to 0 PhI (2.0) 12 77
17[c] CH2Cl2 −40 to 0 PhI (0.5) 46 26
[a]

Yield of combined isolated diastereomers.

[b]

d.r.=87:10:2:<1 as determined by crude 1H NMR spectroscopic and HPLC analyses.

[c]

5.0 equivalents of 1.