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. Author manuscript; available in PMC: 2010 Nov 1.
Published in final edited form as: Org Lett. 2009 Nov 19;11(22):5342–5345. doi: 10.1021/ol9022062

Table 1.

Screening Prins Dimerization/Macrocyclization Conditions

graphic file with name nihms218436t1.jpg
entry catalyst conc time temp yield
1 O3ReOSiPh3
(40 mol %)		 0.10 M 22 h 23 °C 33%
2 O3ReOSiPh3
(50 mol %)		 0.050 M 24 h 23 °C 53%
3 O3ReOSiPh3
(25 mol %) 		0.050 M 24 h 23 °C 51%
4 O3ReOSiPh3
(5 mol %)		 0.050 M 24 h 23 °C 26%
5 aq O3ReOH
(50 mol %)		 0.050 M 24 h 23 °C 29%
6 Re2O7
(50 mol %)		 0.045 M 25 h 23 °C 38%
7 O3ReOSiPh3
(25 mol %)		 0.050 M 5 h 40 °C 51%
8 O3ReOSiPh3
(5 mol %)		 0.050 M 5 h 40 °C 42%
9 TESOTfa
(20 equiv)		 0.030 M 3 h 23 °C 27%b
10 TFA
(20 equiv)		 0.30 M 3 h 23 °C 11%b
a

Run in AcOH with 30 equiv TMSOAc.

b

Yield after hydrolysis of the crude acyl trapped product by MeOH/K2CO3.