Skip to main content
. Author manuscript; available in PMC: 2014 Sep 30.
Published in final edited form as: Synthesis (Stuttg). 2014 Mar 1;46(6):799–808. doi: 10.1055/s-0033-1340565

Table 1.

Optimization of the Reaction Conditionsa

graphic file with name emss-60507-t0005.jpg


graphic file with name emss-60507-t0006.jpg

Entry Catalyst Solvent Timeb (h) Ratio 1a/2a Yieldc (%) of 6a
1 3a CH2Cl2 4.5 1:1 d
2 3a CHCl3 4.5 1:1 d
3 3a toluene 4.5 1:1 d
4 3a DMSO 4.5 1:1 10
5 3a MeOH 4.5 1:1 51
6 3a EtOH 4.5 1:1 50
7 3b EtOH 4.5 1:1 10
8 3c EtOH 4.5 1:1
9 3d EtOH 4.5 1:1
10 3a EtOH 3 1:1 42
11 3a EtOH 8 1:1 46
12 3a EtOH 16 1:1 d
13 3a EtOH 4.5 1:1.5
14 3a EtOH 4.5 1.5:1 65
15 3a EtOH 4.5 2:1 66
a

Unless otherwise noted, all reactions were performed on a 0.33-mmol scale using the indicated ratio of 1a/2a, catalyst (20 mol%), solvent (1.5 mL), r.t., for the indicated time, followed by addition of the Wittig reagent (1.5 equiv) with reaction overnight.

b

Time for the domino reaction before the introduction of the Wittig reagent.

c

Isolated yield.

d

A mixture of 7 and 8 was obtained.